[(5-phenyl-1-heteroaryl-1h-triazol-3-yl)oxy] acetic acid derivatives as safeners for the protection of useful plants and crop plants

ABSTRACT

The present invention relates to crop protection compounds and to compositions which comprise specific compounds as safeners for reducing phytotoxic effects of agrochemicals, especially herbicides.The invention relates more particularly to certain [5-(phenyl)-1-(heteroaryl)-1H-1,2,4-triazol-3-yl)oxy] acetic acid derivatives of the general formula (I)and their salts, to processes for preparing them and to their use as plant protection compounds (safeners).

The present invention relates to useful plant-protecting compounds andcompositions comprising specific compounds as safeners for reduction ofphytotoxic effects of agrochemicals, especially of herbicides. Moreparticularly, the invention relates to particular[(5-phenyl-1-(heteroaryl)-1H-1,2,4-triazol-3-yl)oxy]acetic acidderivatives and salts thereof as safeners and to processes forpreparation thereof.

In the control of unwanted organisms in horticultural and siviculturaluseful plant crops with pesticides, the useful plants are frequentlyalso damaged to a greater or lesser degree by the pesticides used, suchas herbicides, insecticides, fungicides inter alia. This unwantedphytotoxic side effect occurs to a particular degree when numerousherbicides are used—primarily in post-emergence application—in usefulplant crops, for example maize, rice or cereal. The use of “safeners” or“antidotes” can in some cases protect the useful plants against thephytotoxic properties of the pesticides without reducing orsignificantly impairing the pesticidal action with respect to theharmful organisms. In some cases, in the presence of safeners, improvedpesticidal action against harmful organisms such as weeds has even beenobserved.

The compounds that have become known to date as safeners are among alarge number of different chemical structure classes, the suitability ofwhich for use as safeners generally also depends on the chemicalstructures of the pesticides and on the useful plant crops.

Safener effects of compounds from the group of the derivatives ofphenoxy- or heteroaryloxyalkanecarboxylic acids have long been known ifthese compounds are employed in combination with herbicides. Examples ofsuch compounds are MCPA and similar compounds, which at the same timeare still herbicidally active against harmful plants, orcloquintocet-mexyl.

Also known are safeners from the group of the derivatives ofN-phenyl-substituted heteroarylcarboxylic esters with multipleheteroatoms in the heteroaromatic system. Examples of such safeners arethe mefenpyr-diethyl and isoxadifen-ethyl safeners that are used incommercial products.

WO 2004/084631 discloses the use of hydroxy-substituted aromaticcarboxylic acid derivatives. WO 2005/015994 describes specificderivatives of salicylic acid as safeners. These are particularlysuitable for use as safener in maize and soya crops.

In addition, WO 2005/112630 discloses 1,2-dihydroquinoxalin-2-onederivatives, and WO 2008/131860 discloses pyridonecarboxamides assafeners.

Active ingredients from the chemical class of the[(5-phenyl-1-(heteroaryl)-1H-1,2,4-triazol-3-yl)oxy]acetic acidderivatives with plant-active properties are not known from theliterature.

Various documents describe[(1,5-diphenyl-1H-1,2,4-triazol-3-yl)oxy]acetic acid derivatives havingmedical properties. Polish J. Chem. 2006, 80, 889-897 and Bioorganic &Medicinal Chemistry 2018, 26, 3321-3344 disclose[(1,5-diphenyl-1H-1,2,4-triazol-3-yl)oxy] acetic acid derivatives.

When safeners are used for protection of crop plants from damage bypesticides, it has been found that the known safeners can havedisadvantages in many cases. These include:

-   -   the useful plant-protecting properties are inadequate,    -   in combination with a particular herbicide, the spectrum of        useful plants in which the safener/herbicide are to be used is        insufficiently large,    -   a particular safener is combinable with only a few herbicides,    -   the use of safeners increases the application rate to be applied        and amount of formulation auxiliaries, and can thus cause        application-related problems.

For the reasons mentioned, there is an increased need for the provisionof alternative compounds having safener action.

The invention provides novel useful plant-protecting compounds of thegeneral formula (I) or salts thereof

for reduction of phytotoxic effects of pesticides, especially ofherbicides, on useful plants or crop plants,

-   -   in which    -   R¹ is hydrogen, halogen, cyano, nitro, (C₁-C₆)alkyl,        (C₂-C₆)alkenyl, (C₂-C₆)alkynyl, (C₃-C₈)cycloalkyl,        (C₃-C₈)cycloalkenyl, (C₁-C₆)alkoxy and (C₁-C₆)alkylS(O)_(p),        where the latter seven radicals are unsubstituted or are        substituted by one or more radicals from the group of halogen,        cyano, (C₁-C₆)alkoxy and (C₁-C₆)alkylS(O)_(p),    -   R² is heteroaryl, where the heteroaryl radical is an        unsubstituted or substituted by halogen, cyano, nitro,        (C₁-C₆)alkyl, (C₂-C₆)alkenyl, (C₂-C₆)alkynyl, (C₃-C₈)cycloalkyl,        (C₃-C₈)cycloalkenyl, (C₁-C₆)alkoxy and (C₁-C₆)alkylS(O)_(p),        where the latter seven radicals are unsubstituted or are        substituted by one already more radicals from the group of        halogen, cyano, (C₁-C₆)alkoxy and (C₁-C₆)alkylS(O)_(p),    -   R³ is hydrogen and (C₁-C₆)alkyl,    -   R⁴ is hydrogen, (C₁-C₁₈)alkyl, (C₁-C₁₈)halo alkyl,        (C₁-C₁₈)cyanoalkyl, (C₂-C₁₈)alkenyl, (C₂-C₁₈)alkynyl,        (C₃-C₁₂)cyclo alkyl, (C₃-C₁₂)cycloalkenyl, aryl, heteroaryl,        (C₁-C₁₈) alkoxy (C₁-C₁₈)alkyl, (C₁-C₁₈)haloalkoxy-(C₁-C₁₈)alkyl,        (C₁-C₁₈)alkoxy-(C₁-C₁₈)haloalkyl, (C₁-C₁₈)alkyl-thio-(C₁-C₁₈)        alkyl, (C₁-C₁₈)haloalkylthio-(C₁-C₁₈)alkyl, (C₂-C₁₈)haloalkenyl,        (C₂-C₁₈)halo-alkynyl, heterocyclyl-(C₁-C₁₈)alkyl,        aryl-(C₁-C₁₈)alkyl, (C₃-C₁₂)cycloalkyl-(C₁-C₁₈)alkyl,        (C₁-C₁₈)alkoxycarbonyl-(C₁-C₁₈)alkyl, and        (C₁-C₁₈)alkoxycarbonyl-(C₃-C₁₂)cycloalkyl-(C₁-C₁₈)alkyl, or        -   a radical of the formula —NR^(a)R^(b) or —N═CR^(c)R^(d),        -   where, in the former 2 radicals, each of the R^(a), R^(b),            R^(c) and R^(d) radicals is independently hydrogen,            (C₁-C₄)alkyl, (C₂-C₄)alkenyl, (C₂-C₄)alkynyl, benzyl,            substituted benzyl, phenyl or substituted phenyl, or R^(a)            and R^(b) together with the nitrogen atom may form a 3- to            8-membered heterocycle which may contain one or two further            ring heteroatoms from the group of N, O and S, but not in            the case of a 3- or 4-membered heterocycle, and which is            unsubstituted or substituted by one or more radicals from            the group of (C₁-C₄)alkyl and (C₁-C₄)haloalkyl, or R^(c) and            R^(d) together with the carbon atom are a 3- to 8-membered            carbocyclic or heterocyclic radical which may contain 1 to 3            ring heteroatoms from the group of N, O and S, where the            carbocyclic or heterocyclic radical is unsubstituted or            substituted by one or more radicals from the group of            (C₁-C₄)-alkyl and (C₁-C₄)-haloalkyl,    -   n is a number from 0 to 5,    -   and    -   p is 0, 1 or 2.

The compounds of the general formula (I) can form salts by addition of asuitable inorganic or organic acid, for example mineral acids, forexample HCl, HBr, H₂SO₄, H₃PO₄ or HNO₃, or organic acids, for examplecarboxylic acids such as formic acid, acetic acid, propionic acid,oxalic acid, lactic acid or salicylic acid or sulfonic acids, forexample p-toluenesulfonic acid, onto a basic group, for example amino,alkylamino, dialkylamino, piperidino, morpholino or pyridino. Thesesalts then contain the conjugate base of the acid as anion. Suitablesubstituents in deprotonated form, for example sulfonic acids,particular sulfonamides or carboxylic acids, are capable of forminginternal salts with groups, such as amino groups, which are themselvesprotonatable. Salts may also be formed by action of a base on compoundsof the general formula (I). Suitable bases are, for example, organicamines such as trialkylamines, morpholine, piperidine and pyridine, andthe hydroxides, carbonates and hydrogencarbonates of ammonium, alkalimetals or alkaline earth metals, especially sodium hydroxide, potassiumhydroxide, sodium carbonate, potassium carbonate, sodiumhydrogencarbonate and potassium hydrogencarbonate. These salts arecompounds in which the acidic hydrogen is replaced by an agriculturallysuitable cation, for example metal salts, especially alkali metal saltsor alkaline earth metal salts, in particular sodium and potassium salts,or else ammonium salts, salts with organic amines or quaternary ammoniumsalts, for example with cations of the formula[NR^(i)R^(ii)R^(iii)R^(iv)]⁺ in which R^(i) to R^(iv) are eachindependently an organic radical, especially alkyl, aryl, arylalkyl oralkylaryl. Also useful are alkylsulfonium and alkylsulfoxonium salts,such as (C₁-C₄)-trialkylsulfonium and (C₁-C₄)-trialkylsulfoxonium salts.

The compounds of the formula (I) used in accordance with the inventionand salts thereof are referred to hereinafter as “compounds of thegeneral formula (I)”.

The invention preferably provides compounds of the general formula (I)in which

-   -   R¹ is hydrogen, halogen, cyano, nitro, (C₁-C₄)alkyl,        (C₂-C₄)alkenyl, (C₂-C₄)alkynyl, (C₃-C₆)cycloalkyl,        (C₃-C₆)cycloalkenyl, (C₁-C₄)alkoxy and (C₁-C₄)alkylS(O)_(p),        where the latter seven radicals are unsubstituted or are        substituted by one already more radicals from the group of        halogen, cyano, (C₁-C₄)alkoxy and (C₁-C₄)alkylS(O)_(p),    -   R² is heteroaryl, where the heteroaryl radical is unsubstituted        or substituted by halogen, cyano, nitro, (C₁-C₆)alkyl,        (C₂-C₆)alkenyl, (C₂-C₄)alkynyl, (C₃-C₆)cycloalkyl,        (C₃-C₆)cycloalkenyl, (C₁-C₄)alkoxy and (C₁-C₄)alkylS(O)_(p),        where the latter seven radicals are unsubstituted or are        substituted by one already more radicals from the group of        halogen, cyano, (C₁-C₄)alkoxy and (C₁-C₄)alkylS(O)_(p),    -   R³ is hydrogen and (C₁-C₄)alkyl,    -   R⁴ is hydrogen, (C₁-C₁₆)alkyl, (C₁-C₁₆)halo alkyl,        (C₁-C₁₆)cyanoalkyl, (C₂-C₁₆)alkenyl, (C₂-C₁₆)alkynyl,        (C₃-C₁₂)cycloalkyl, (C₃-C₁₂)cycloalkenyl, aryl, heteroaryl,        (C₁-C₁₆)alkoxy-(C₁-C₁₆)alkyl, (C₁-C₁₆)haloalkoxy-(C₁-C₁₆)alkyl,        (C₁-C₁₆)alkoxy-(C₁-C₁₆)haloalkyl, (C₁-C₁₆)alkyl-thio-(C i-C₁₆)        alkyl, (C₁-C₁₆)haloalkylthio-(C₁-C₁₆)alkyl, (C₂-C₁₆)haloalkenyl,        (C₂-C₁₆)halo-35 alkynyl, heterocyclyl-(C₁-C₁₆)alkyl,        aryl-(C₁-C₁₆)alkyl, (C₃-C₁₂)cycloalkyl-(C₁-C₁₆)alkyl,        (C₁-C₁₆)alkoxycarbonyl-(C₁-C₁₆)alkyl, and        (C₁-C₁₆)alkoxycarbonyl-(C₃-C₁₂)cycloalkyl-(C₁-C₁₆)alkyl,    -   n is a number from 0 to 4,    -   and    -   p is 0, 1 or 2.

The invention very particularly preferably provides compounds of thegeneral formula (I) in which

-   -   R¹ is hydrogen, halogen, cyano, methyl, ethyl, CF₃, CF₂ Cl,        CH₂F, CHF₂, OCH₃, OCF₃, SCH₃, SOCH₃, SO₂CH₃ and SCF₃,    -   R² is heteroaryl, where the heteroaryl radical is unsubstituted        or mono- or polysubstituted by halogen, cyano, methyl, ethyl,        CF₃, CF₂Cl, CH₂F, CHF₂, OCH₃, OCF₃, SCH₃, SOCH₃, SO₂CH₃ and        SCF₃,    -   R³ is hydrogen, CH₂CH₃ and CH₃,    -   R⁴ is hydrogen, (C₁-C₁₂)alkyl, (C₁-C₁₂)halo alkyl,        (C₁-C₁₂)cyanoalkyl, (C₂-C₁₂)alkenyl, (C₂-C₁₂)alkynyl,        (C₃-C₁₂)cycloalkyl, (C₃-C₁₂)cycloalkenyl, aryl, heteroaryl,        (C₁-C₁₂)alkoxy-(C₁-C₁₂)alkyl, (C₁-C₁₂)haloalkoxy-(C₁-C₁₂)alkyl,        (C₁-C₁₂)alkoxy-(C₁-C₁₂)haloalkyl,        (C₁-C₁₂)alkyl-thio-(C₁-C₁₂)alkyl,        (C₁-C₁₂)haloalkylthio-(C₁-C₁₂)alkyl, (C₂-C₁₂)haloalkenyl,        (C₂-C₁₂)halo-alkynyl, heterocyclyl-(C₁-C₁₂)alkyl,        aryl-(C₁-C₁₂)alkyl, (C₃-C₁₂)cycloalkyl-(C₁-C₁₂)alkyl,        (C₁-C₁₂)alkoxycarbonyl-(C₁-C₁₂)alkyl, and        (C₁-C₁₂)alkoxycarbonyl-(C₃-C₁₂)cycloalkyl-(C₁-C₁₂)alkyl,    -   and    -   n is 0, 1, 2 or 3.

The invention especially preferably provides compounds of the generalformula (I) in which

-   -   R¹ is hydrogen, fluorine, chlorine, bromine, iodine, CN, methyl,        ethyl, CF₃, CF₂ Cl, CH₂F, CHF₂, OCH₃, OCF₃, SCH₃, SOCH₃, SO₂CH₃        and SCF₃,    -   R² is pyridin-2-yl, pyridin-3-yl, pyridin-4-yl, pyrazin-2-yl,        pyrazin-3-yl, pyrimidin-2-yl, pyrimidin-4-yl, pyrimidin-5-yl,        pyridazin-3-yl, pyridazin-4-yl, 1,3,5-triazin-2-yl,        1,2,4-triazin-3-yl, 1,2,4-triazin-5-yl, 1,2,4-triazin-6-yl,        1,2,3-triazin-4-yl, 1,2,3-triazin-5-yl, 1,2,4-, 1,3,2-, 1,3,6-        and 1,2,6-oxazinyl, isoxazol-3-yl, isoxazol-4-yl, isoxazol-5-yl,        1,3-oxazol-2-yl, 1,3-oxazol-4-yl, 1,3-oxazol-5-yl,        isothiazol-3-yl, isothiazol-4-yl, isothiazol-5-yl,        1,3-thiazol-2-yl, 1,3-thiazol-4-yl, 1,3-thiazol-5-yl,        1H-pyrrol-1-yl; 1H-pyrrol-2-yl; 1H-pyrrol-3-yl, furan-2-yl;        furan-3-yl, thien-2-yl, thien-3-yl, 1H-imidazol-1-yl,        1H-imidazol-2-yl, 1H-imidazol-4-yl, 1H-imidazol-5-yl,        1H-pyrazol-1-yl, 1H-pyrazol-3-yl, 1H-pyrazol-4-yl,        1H-pyrazol-5-yl, 1H-1,2,3-triazol-1-yl, 1H-1,2,3-triazol-4-yl,        1H-1,2,3-triazol-5-yl, 2H-1,2,3-triazol-2-yl,        2H-1,2,3-triazol-4-yl, 1H-1,2,4-triazol-1-yl,        1H-1,2,4-triazol-5-yl, 4H-1,2,4-triazol-3-yl,        1,2,4-oxadiazol-3-yl, 1,2,4-oxadiazol-5-yl,        1,3,4-oxadiazol-2-yl, 1,2,3-oxadiazol-4-yl,        1,2,3-oxadiazol-5-yl, 1,2,5-oxadiazol-3-yl,        1,3,4-thiadiazol-2-yl, 1,3,4-thiadiazol-2-yl,        1,2,4-thiadiazol-5-yl, 1,2,4-thiadiazol-3-yl,        1,2,5-thiadiazol-3-yl, 1,2,5-thiadiazol-3-yl,        1,2,3-thiadiazol-4-yl, 1,2,3-thiadiazol-3-yl, which is        unsubstituted or mono- or polysubstituted by halogen, cyano,        methyl, CF₃, CF₂Cl, CH₂F, CHF₂, OCH₃, OCF₃, SCH₃, SOCH₃, SO₂CH₃        and SCF₃,    -   R³ is hydrogen and CH₃,    -   R⁴ is hydrogen, (C₁-C₁₀)alkyl, (C₁-C₁₀)haloalkyl,        (C₁-C₁₀)cyanoalkyl, (C₂-C₁₀)alkenyl, (C₂-C₁₀)alkynyl,        (C₃-C₉)cycloalkyl, (C₃-C₉)cycloalkenyl, aryl, heteroaryl,        (C₁-C₁₀)alkoxy-(C₁-C₁₀)alkyl, (C₁-C₁₀)haloalkoxy-(C₁-C₁₀)alkyl,        (C₁-C₁₀)alkoxy-(C₁-C₁₀)haloalkyl, (C₁-C₁₀)alkyl-thio-(C₁-C₁₀)        alkyl, (C₁-C₁₀)haloalkylthio-(C₁-C₁₀)alkyl, (C₂-C₁₈)haloalkenyl,        (C₂-C₁₈)halo-alkynyl, heterocyclyl-(C₁-C₁₀)alkyl,        aryl-(C₁-C₁₀)alkyl, (C₃-C₉)cycloalkyl-(C₁-C₁₀)alkyl,        (C₁-C₁₀)alkoxycarbonyl-(C₁-C₁₀)alkyl and        (C₁-C₁₀)alkoxycarbonyl-(C₃-C₉)cyclo alkyl-(C₁-C₁₀)alkyl,    -   and    -   n is 0, 1, 2 or 3.

The invention very especially preferably provides compounds of thegeneral formula (I) in which

-   -   R¹ is hydrogen, fluorine, chlorine, bromine, iodine, cyano,        methyl, CF₃, CH₂F, CHF₂, OCH₃, OCF₃, SCH₃, SOCH₃, SO₂CH₃ and        SCF₃,    -   R² is the groups Q-2.1 to Q-2.60

-   -   R³ is hydrogen,    -   R⁴ is hydrogen, methyl, ethyl, n-propyl, i-propyl, n-butyl,        n-pentyl, phenyl, benzyl, CH₂(4-Cl-Ph), CH₂(4-F-Ph),        CH₂(4-MeO-Ph), 2-methoxyethyl, tetrahydrofuran-2-yl-methyl,        tetrahydrofuran-3-ylmethyl, tetrahydropyran-2-ylmethyl,        tetrahydropyran-3-ylmethyl, tetrahydropyran-4-ylmethyl,        methylpropionate-3-yl, ethylpropionate-3-yl, methylacetate-2-yl,        ethylacetate-2-yl, methyl-pivalate-2-yl, ethylpivalate-3-yl,        methyl-2-methylpropanoate-3-yl,        methyl-2,2-dimethyl-propanoate-3-yl,        ethyl-2-methylpropanoate-3-yl, methyl-2-propanoate-2-yl,        ethyl-2-propanoate-2-yl, methylacetate-2-yl, ethylacetate-2-yl,        methyl-1-methylcyclopropanecarboxylate-2-yl,        ethyl-1-methylcyclopropanecarboxylat-2-yl,        2-(dimethylamino)ethyl, oxetan-3-yl,        (3-methyloxetan-3-yl)methyl, 2,2,2-trifluoroethyl,        2,2-difluoroethyl, 2-fluoroethyl, 2,2,3,3,3-pentafluoropropyl,        cyclopropylmethyl, 1-cyclopropylethyl,        (1-methylcyclopropyl)methyl, (2,2-dichlorocyclo-propyl)methyl,        (2,2-dimethylcyclopropyl)methyl, allyl, propargyl        (prop-2-yn-1-yl), 2-chloro-prop-2-en-1-yl,        3-phenylprop-2-yn-1-yl, 3,3-dichloroprop-2-en-1-yl,        3,3-dichloro-2-fluoroprop-2-en-1-yl, methylprop-2-yn-1-yl,        2-methylprop-2-en-1-yl, but-2-en-1-yl, but-3-en-1-yl,        but-2-yn-1-yl, but-3-yn-1-yl, 4-chlorobut-2-yn-1-yl,        3-methylbut-2-en-1-yl, 3-methylbut-1-en-1-yl,        1-(2E)-1-methylbut-2-en-1-yl, (E)-pent-3-en-2-yl or        (Z)-pent-3-en-2-yl, cyclobutylmethyl, cyclo-pentylmethyl,        cyclohexylmethyl, heptan-2-yl, isobutyl, 1,3-dioxolan-2-ylmethyl        or 1-ethyl-5-methyl-1H-pyrazole-4-methyl,    -   n is 0, 1, 2 or 3.

The invention extremely especially preferably provides compounds of thegeneral formula (I) in which (R¹)_(n)-phenyl is the groups Q-1.1 toQ-1.53

-   -   and    -   R² is the groups Q-2.1 to Q-2.60

-   -   R³ is hydrogen,    -   and    -   R⁴ is hydrogen, methyl, ethyl, n-propyl, i-propyl, n-butyl,        n-pentyl, phenyl, benzyl, CH₂(4-Cl-Ph), CH₂(4-F-Ph),        CH₂(4-MeO-Ph), 2-methoxyethyl, tetrahydrofuran-2-yl-methyl,        tetrahydrofuran-3-ylmethyl, tetrahydropyran-2-ylmethyl,        tetrahydropyran-3-ylmethyl, tetrahydropyran-4-ylmethyl,        methylpropionate-3-yl, ethylpropionate-3-yl, methylacetate-2-yl,        ethylacetate-2-yl, methyl-pivalate-2-yl, ethylpivalate-3-yl,        methyl-2-methylpropanoate-3-yl,        methyl-2,2-dimethyl-propanoate-3-yl,        ethyl-2-methylpropanoate-3-yl, methyl-2-propanoate-2-yl,        ethyl-2-propanoate-2-yl, methylacet-2-yl, ethylacet-2-yl,        methyl-1-methylcyclopropanecarboxylate-2-yl,        ethyl-1-methylcyclopropanecarboxylat-2-yl,        2-(dimethylamino)ethyl, oxetan-3-yl,        (3-methyloxetan-3-yl)methyl, 2,2,2-trifluoroethyl,        2,2-difluoroethyl, 2-fluoroethyl, 2,2,3,3,3-pentafluoropropyl,        cyclopropylmethyl, 1-cyclopropylethyl,        (1-methylcyclopropyl)methyl, (2,2-dichloro-cyclopropyl)methyl,        (2,2-dimethylcyclopropyl)methyl, allyl, propargyl        (prop-2-yn-1-yl), 2-chloroprop-2-en-1-yl,        3-phenylprop-2-yn-1-yl, 3,3-dichloroprop-2-en-1-yl,        3,3-dichloro-2-fluoroprop-2-en-1-yl, methylprop-2-yn-1-yl,        2-methylprop-2-en-1-yl, but-2-en-1-yl, but-3-en-1-yl,        but-2-yn-1-yl, but-3-yn-1-yl, 4-chlorobut-2-yn-1-yl,        3-methylbut-2-en-1-yl, 3-methylbut-1-en-1-yl,        1-(2E)-1-methylbut-2-en-1-yl, (E)-pent-3-en-2-yl or        (Z)-pent-3-en-2-yl, cyclo-butylmethyl, cyclopentylmethyl,        cyclohexylmethyl, heptan-2-yl, isobutyl, 1,3-dioxolan-2-ylmethyl        or 1-ethyl-5-methyl-1H-pyrazole-4-methyl.

The invention particularly extremely especially preferably providescompounds of the general formula (I) in which

-   -   (R¹)_(n)-phenyl is the groups Q-1.1 to Q-1.53

-   -   and    -   R² is the groups Q-2.1 to Q-2.60

-   -   R³ is hydrogen,    -   and    -   R⁴ is hydrogen, methyl, ethyl, n-propyl, i-propyl, n-butyl,        n-pentyl, phenyl, benzyl, CH₂(4-Cl-Ph), CH₂(4-F-Ph),        CH₂(4-MeO-Ph), 2-methoxyethyl, tetrahydrofuran-2-yl-methyl,        tetrahydrofuran-3-ylmethyl, tetrahydropyran-2-ylmethyl,        tetrahydropyran-3-ylmethyl, tetrahydropyran-4-ylmethyl,        methylpropionate-3-yl, ethylpropionate-3-yl, methylacetate-2-yl,        ethylacetate-2-yl, methyl-pivalate-2-yl, ethylpivalate-3-yl,        methyl-2-methylpropanoate-3-yl,        methyl-2,2-dimethylpropanoate-3-yl,        ethyl-2-methylpropanoate-3-yl, methyl-2-propanoate-2-yl,        ethyl-2-propanoate-2-yl, methylacet-2-yl, ethylacet-2-yl,        methyl-1-methylcyclopropanecarboxylate-2-yl,        ethyl-1-methylcyclopropanecarboxylat-2-yl,        2-(dimethylamino)ethyl, oxetan-3-yl,        (3-methyloxetan-3-yl)methyl, 2,2,2-trifluoroethyl,        2,2-difluoroethyl, 2-fluoroethyl, 2,2,3,3,3-penta-fluoropropyl,        cyclopropylmethyl, 1-cyclopropylethyl,        (1-methylcyclopropyl)methyl, (2,2-dichlorocyclopropyl)methyl,        (2,2-dimethylcyclopropyl)methyl, allyl, propargyl        (prop-2-yn-1-yl), 2-chloroprop-2-en-1-yl,        3-phenylprop-2-yn-1-yl, 3,3-dichloroprop-2-en-1-yl,        3,3-dichloro-2-fluoroprop-2-en-1-yl, methylprop-2-yn-1-yl,        2-methylprop-2-en-1-yl, but-2-en-1-yl, but-3-en-1-yl,        but-2-yn-1-yl, but-3-yn-1-yl, 4-chlorobut-2-yn-1-yl,        3-methylbut-2-en-1-yl, 3-methylbut-1-en-1-yl,        1-(2E)-1-methylbut-2-en-1-yl, (E)-pent-3-en-2-yl or        (Z)-pent-3-en-2-yl, cyclobutyl-methyl, cyclopentylmethyl,        cyclohexylmethyl, heptan-2-yl, isobutyl, 1,3-dioxolan-2-ylmethyl        or 1-ethyl-5-methyl-1H-pyrazole-4-methyl.

The abovementioned general or preferred radical definitions apply bothto the end products of the general formula (I) and, correspondingly, tothe starting materials or the intermediates required in each case forthe preparation. These radical definitions can be combined with oneanother as desired, i.e. including combinations between the givenpreferred ranges.

Of particular interest, primarily for reasons of higher herbicidalactivity, better selectivity and/or better preparability, are inventivecompounds of the general formula (I) given or salts thereof or theinventive use thereof in which individual radicals have one of thepreferred meanings already specified or specified below, or inparticular those in which one or more of the preferred meanings alreadyspecified or specified below occur in combination.

With regard to the compounds of the invention, the terms used above andfurther down will be elucidated. These are familiar to the personskilled in the art and especially have the definitions elucidatedhereinafter:

Unless defined differently, names of chemical groups are generally to beunderstood such that attachment to the skeleton or the remainder of themolecule is via the structural element of the relevant chemical groupmentioned last, i.e. for example in the case of (C₂-C₁₈)-alkenyloxy viathe oxygen atom and in the case of heterocyclyl-(C₁-C₁₈)-alkyl orMeO(O)C—(C₁-C₁₈)-alkyl in each case via the carbon atom of the alkylgroup.

According to the invention, “alkylsulfonyl”—alone or as part of achemical group—refers to straight-chain or branched alkylsulfonyl,preferably having 1 to 8 or 1 to 6 carbon atoms, for example (but notlimited to) (C₁-C₆)-alkylsulfonyl such as methylsulfonyl, ethylsulfonyl,propylsulfonyl, 1-methylethylsulfonyl, butylsulfonyl,1-methylpropylsulfonyl, 2-methylpropylsulfonyl,1,1-dimethylethylsulfonyl, pentyl-sulfonyl, 1-methylbutylsulfonyl,2-methylbutylsulfonyl, 3-methylbutylsulfonyl,1,1-dimethylpropyl-sulfonyl, 1,2-dimethylpropylsulfonyl,2,2-dimethylpropylsulfonyl, 1-ethylpropylsulfonyl, hexylsulfonyl,1-methylpentylsulfonyl, 2-methylpentylsulfonyl, 3-methylpentylsulfonyl,4-methylpentylsulfonyl, 1,1-dimethylbutylsulfonyl,1,2-dimethylbutylsulfonyl, 1,3-dimethylbutylsulfonyl,2,2-dimethylbutylsulfonyl, 2,3-dimethylbutylsulfonyl,3,3-dimethylbutylsulfonyl, 1-ethylbutylsulfonyl, 2-ethylbutylsulfonyl,1,1,2-trimethylpropylsulfonyl, 1,2,2-trimethylpropylsulfonyl,1-ethyl-1-methylpropylsulfonyl and 1-ethyl-2-methylpropylsulfonyl.

According to the invention, “alkylthio”—alone or as part of a chemicalgroup—refers to straight-chain or branched S-alkyl, preferably having 1to 8 or 1 to 6 carbon atoms, such as (C₁-C₁₀)—, (C₁-C₆)- or(C₁-C₄)-alkylthio, for example (but not limited to) (C₁-C₆)-alkylthiosuch as methylthio, ethylthio, propylthio, 1-methylethylthio, butylthio,1-methylpropylthio, 2-methylpropylthio, 1,1-dimethylethylthio,pentylthio, 1-methylbutylthio, 2-methylbutylthio, 3-methylbutylthio,1,1-dimethylpropylthio, 1,2-dimethylpropylthio, 2,2-dimethylpropylthio,1-ethylpropylthio, hexylthio, 1-methylpentylthio, 2-methylpentylthio,3-methylpentylthio, 4-methylpentylthio, 1,1-dimethylbutylthio,1,2-dimethylbutylthio, 1,3-dimethyl-butylthio, 2,2-dimethylbutylthio,2,3-dimethylbutylthio, 3,3-dimethylbutylthio, 1-ethylbutylthio,2-ethylbutylthio, 1,1,2-trimethylpropylthio, 1,2,2-trimethylpropylthio,1-ethyl-1-methylpropylthio and 1-ethyl-2-methylpropylthio.

According to the invention, “alkylsulfinyl (alkyl-S(═O)—)”, unlessdefined differently elsewhere, denotes alkyl radicals which are bondedto the skeleton via —S(═O)—, such as (C₁-C₁₀)—, (C₁-C₆)- or(C₁-C₄)-alkylsulfinyl, for example (but not limited to)(C₁-C₆)-alkylsulfinyl such as methylsulfinyl, ethylsulfinyl,propylsulfinyl, 1-methylethylsulfinyl, butylsulfinyl,1-methylpropylsulfinyl, 2-methylpropylsulfinyl,1,1-dimethylethylsulfinyl, pentylsulfinyl, 1-methylbutylsulfinyl,2-methylbutylsulfinyl, 3-methylbutyl-sulfinyl,1,1-dimethylpropylsulfinyl, 1,2-dimethylpropylsulfinyl,2,2-dimethylpropylsulfinyl, 1-ethyl-propylsulfinyl, hexylsulfinyl,1-methylpentylsulfinyl, 2-methylpentylsulfinyl, 3-methylpentylsulfinyl,4-methylpentylsulfinyl, 1,1-dimethylbutylsulfinyl,1,2-dimethylbutylsulfinyl, 1,3-dimethylbutylsulfinyl,2,2-dimethylbutylsulfinyl, 2,3-dimethylbutylsulfinyl,3,3-dimethylbutylsulfinyl, 1-ethylbutylsulfinyl, 2-ethyl-butylsulfinyl,1,1,2-trimethylpropylsulfinyl, 1,2,2-trimethylpropylsulfinyl,1-ethyl-1-methylpropyl-sulfinyl and 1-ethyl-2-methylpropylsulfinyl.

“Alkoxy” denotes an alkyl radical attached via an oxygen atom, forexample (but not limited to) (C₁-C₆)-alkoxy such as methoxy, ethoxy,propoxy, 1-methylethoxy, butoxy, 1-methylpropoxy, 2-methylpropoxy,1,1-dimethylethoxy, pentoxy, 1-methylbutoxy, 2-methylbutoxy,3-methylbutoxy, 1,1-dimethylpropoxy, 1,2-dimethylpropoxy,2,2-dimethylpropoxy, 1-ethylpropoxy, hexoxy, 1-methylpentoxy,2-methylpentoxy, 3-methylpentoxy, 4-methylpentoxy, 1,1-dimethylbutoxy,1,2-dimethylbutoxy, 1,3-dimethylbutoxy, 2,2-dimethylbutoxy,2,3-dimethylbutoxy, 3,3-dimethylbutoxy, 1-ethylbutoxy, 2-ethylbutoxy,1,1,2-trimethylpropoxy, 1,2,2-trimethylpropoxy, 1-ethyl-1-methylpropoxyand 1-ethyl-2-methylpropoxy. Alkenyloxy denotes an alkenyl radicalattached via an oxygen atom, and alkynyloxy denotes an alkynyl radicalattached via an oxygen atom, such as (C₂-C₁₀-, (C₂-C₆)- or(C₂-C₄)-alkeneoxy and (C₃-C₁₀)—, (C₃-C₆)- or (C₃-C₄)-alkyneoxy.

According to the invention, “alkylcarbonyl” (alkyl-C(═O)—), unlessdefined differently elsewhere, represents alkyl radicals bonded to theskeleton via —C(═O)—, such as (C₁-C₁₀)-, (C₁-C₆)- or(C₁-C₄)-alkylcarbonyl. The number of the carbon atoms here relates tothe alkyl radical in the alkylcarbonyl group.

“Alkoxycarbonyl (alkyl-O—C(═O)—)”, unless defined differently elsewhere:alkyl radicals bonded to the skeleton via —O—C(═O)—, such as (C₁-C₁₀)—,(C₁-C₆)- or (C₁-C₄)-alkoxycarbonyl. The number of the carbon atoms hererelates to the alkyl radical in the alkoxycarbonyl group. Analogously,“alkenyloxycarbonyl” and “alkynyloxycarbonyl”, unless defineddifferently elsewhere, in accordance with the invention, respectivelyrepresent alkenyl and alkynyl radicals bonded to the skeleton via—O—C(═O)—, such as (C₂-C₆)- or (C₂-C₄)-alkenyloxycarbonyl and (C₃-C₁₀)—,(C₃-C₆)- or (C₃-C₄)-alkynyloxycarbonyl. The number of the carbon atomshere refers to the alkenyl or alkynyl radical in the alkenyloxycarbonylor alkynyloxycarbonyl group.

According to the invention, the term “alkylcarbonyloxy”(alkyl-C(═O)—O—), unless defined differently elsewhere, represents alkylradicals bonded to the skeleton via the oxygen of a carbonyloxy group(—C(═O)—O—), such as (C₁-C₁₀)—, (C₁-C₆)- or (C₁-C₄)-alkylcarbonyloxy.The number of the carbon atoms here relates to the alkyl radical in thealkylcarbonyloxy group.

The term “aryl” denotes an optionally substituted mono-, bi- orpolycyclic aromatic system having preferably 6 to 14, especially 6 to10, ring carbon atoms, for example phenyl, naphthyl, anthryl,phenanthrenyl and the like, preferably phenyl.

The term “optionally substituted aryl” also includes polycyclic systems,such as tetrahydronaphthyl, indenyl, indanyl, fluorenyl, biphenylyl,where the bonding site is on the aromatic system. In systematic terms,“aryl” is generally also encompassed by the term “optionally substitutedphenyl”. Preferred aryl substituents here are, for example, hydrogen,halogen, alkyl, cycloalkyl, cycloalkylalkyl, cycloalkenyl,halocycloalkyl, alkenyl, alkynyl, aryl, arylalkyl, heteroaryl,heteroarylalkyl, heterocyclyl, heterocyclylalkyl, alkoxyalkyl,alkylthio, haloalkylthio, haloalkyl, alkoxy, haloalkoxy, cycloalkoxy,cycloalkylalkoxy, aryloxy, heteroraryloxy, alkoxyalkoxy, alkynylalkoxy,alkenyloxy, bisalkylaminoalkoxy, tris [alkyl]silyl, bis[alkyl]arylsilyl, bis [alkyl]alkylsilyl, tris [alkyl]silyl alkynyl,alkylalkynyl, cycloalkylalkynyl, haloalkylalkynyl,heterocyclyl-N-alkoxy, nitro, cyano, amino, alkylamino, bisalkylamino,alkylcarbonylamino, cycloalkylcarbonylamino, arylcarbonylamino,alkoxycarbonylamino, alkoxycarbonylalkylamino,arylalkoxycarbonylalkylamino, hydroxycarbonyl, alkoxycarbonyl,aminocarbonyl, alkylaminocarbonyl, cycloalkylaminocarbonyl,bisalkylaminocarbonyl, heteroarylalkoxy, arylalkoxy.

A heterocyclic radical (heterocyclyl) contains at least one heterocyclicring (=carbocyclic ring in which at least one carbon atom has beenreplaced by a heteroatom, preferably by a heteroatom from the group ofN, O, S, P) which is saturated, unsaturated, partly saturated orheteroaromatic and may be unsubstituted or substituted, in which casethe bonding site is localized on a ring atom. If the heterocyclylradical or the heterocyclic ring is optionally substituted, it may befused to other carbocyclic or heterocyclic rings. In the case ofoptionally substituted heterocyclyl, polycyclic systems are alsoincluded, for example 8-azabicyclo[3.2.1]octanyl,8-azabicyclo[2.2.2]octanyl or 1-azabicyclo[2.2.1]heptyl. Optionallysubstituted heterocyclyl also includes spirocyclic systems, for example1-oxa-5-azaspiro[2.3]hexyl. Unless defined differently, the heterocyclicring preferably contains 3 to 9 ring atoms, especially 3 to 6 ringatoms, and one or more, preferably 1 to 4, especially 1, 2 or 3,heteroatoms in the heterocyclic ring, preferably from the group of N, Oand S, but no two oxygen atoms should be directly adjacent, for examplewith one heteroatom from the group of N, O and S: 1- or 2- or3-pyrrolidinyl, 3,4-dihydro-2H-pyrrol-2- or -3-yl,2,3-dihydro-1H-pyrrol-1- or -2- or -3- or -4- or -5-yl;2,5-dihydro-1H-pyrrol-1- or -2- or -3-yl, 1- or 2- or 3- or4-piperidinyl; 2,3,4,5-tetrahydropyridin-2- or -3- or -4- or -5-yl or-6-yl; 1,2,3,6-tetrahydropyridin-1- or -2- or -3- or -4- or -5- or-6-yl; 1,2,3,4-tetrahydropyridin-1- or -2- or -3- or -4- or -5- or-6-yl; 1,4-dihydropyridin-1- or -2- or -3- or -4-yl;2,3-dihydropyridin-2- or -3- or -4- or -5- or -6-yl;2,5-dihydropyridin-2- or -3- or -4- or -5- or -6-yl, 1- or 2- or 3- or4-azepanyl; 2,3,4,5-tetrahydro-1H-azepin-1- or -2- or -3- or -4- or -5-or -6- or -7-yl; 2,3,4,7-tetrahydro-1H-azepin-1- or -2- or -3- or -4- or-5- or -6- or -7-yl; 2,3,6,7-tetrahydro-1H-azepin-1- or -2- or -3- or-4-yl; 3,4,5,6-tetrahydro-2H-azepin-2- or -3- or -4- or -5- or -6- or-7-yl; 4,5-dihydro-1H-azepin-1- or -2- or -3- or -4-yl;2,5-dihydro-1H-azepin-1- or -2- or -3- or -4- or -5- or -6- or -7-yl;2,7-dihydro-1H-azepin-1- or -2- or -3- or -4-yl;2,3-dihydro-1H-azepin-1- or -2- or -3- or -4- or -5- or -6- or -7-yl;3,4-dihydro-2H-azepin-2- or -3- or -4- or -5- or -6- or -7-yl;3,6-dihydro-2H-azepin-2- or -3- or -4- or -5- or -6- or -7-yl;5,6-dihydro-2H-azepin-2- or -3- or -4- or -5- or -6- or -7-yl;4,5-dihydro-3H-azepin-2- or -3- or -4- or -5- or -6- or -7-yl;1H-azepin-1- or -2- or -3- or -4- or -5- or -6- or -7-yl; 2H-azepin-2-or -3- or -4- or -5- or -6- or -7-yl; 3H-azepin-2- or -3- or -4- or -5-or -6- or -7-yl; 4H-azepin-2- or -3- or -4- or -5- or -6- or -7-yl, 2-or 3-oxolanyl (=2- or 3-tetrahydrofuranyl); 2,3-dihydrofuran-2- or -3-or -4- or -5-yl; 2,5-dihydrofuran-2- or -3-yl, 2- or 3- or 4-oxanyl (=2-or 3- or 4-tetrahydropyranyl); 3,4-dihydro-2H-pyran-2- or -3- or -4- or-5- or -6-yl; 3,6-dihydro-2H-pyran-2- or -3- or -4- or -5- or -6-yl;2H-pyran-2- or -3- or -4- or -5- or -6-yl; 4H-pyran-2- or -3- or -4-yl,2- or 3- or 4-oxepanyl; 2,3,4,5-tetrahydrooxepin-2- or -3- or -4- or -5-or -6- or -7-yl; 2,3,4,7-tetrahydrooxepin-2- or -3- or -4- or -5- or -6-or -7-yl; 2,3,6,7-tetrahydrooxepin-2- or -3- or -4-yl;2,3-dihydrooxepin-2- or -3- or -4- or -5- or -6- or -7-yl;4,5-dihydrooxepin-2- or -3- or -4-yl; 2,5-dihydrooxepin-2- or -3- or -4-or -5- or -6- or -7-yl; oxepin-2- or -3- or -4- or -5- or -6- or -7-yl;2- or 3-tetrahydrothiophenyl; 2,3-dihydrothiophen-2- or -3- or -4- or-5-yl; 2,5-dihydrothiophen-2- or -3-yl; tetrahydro-2H-thiopyran-2- or-3- or -4-yl; 3,4-dihydro-2H-thiopyran-2- or -3- or -4- or -5- or -6-yl;3,6-dihydro-2H-thiopyran-2- or -3- or -4- or -5- or -6-yl;2H-thiopyran-2- or -3- or -4- or -5- or -6-yl; 4H-thiopyran-2- or -3- or-4-yl. Preferred 3-membered and 4-membered heterocycles are, forexample, 1- or 2-aziridinyl, oxiranyl, thiiranyl, 1- or 2- or3-azetidinyl, 2- or 3-oxetanyl, 2- or 3-thietanyl, 1,3-dioxetan-2-yl.Further examples of “heterocyclyl” are a partly or fully hydrogenatedheterocyclic radical having two heteroatoms from the group of N, O andS, for example 1- or 2- or 3- or 4-pyrazolidinyl;4,5-dihydro-3H-pyrazol-3- or 4- or 5-yl; 4,5-dihydro-1H-pyrazol-1- or 3-or 4- or 5-yl; 2,3-dihydro-1H-pyrazol-1- or 2- or 3- or 4- or 5-yl; 1-or 2- or 3- or 4-imidazolidinyl; 2,3-dihydro-1H-imidazol-1- or 2- or 3-or 4-yl; 2,5-dihydro-1H-imidazol-1- or 2- or 4- or 5-yl;4,5-dihydro-1H-imidazol-1- or 2- or 4- or 5-yl; hexahydropyridazin-1- or2- or 3- or 4-yl; 1,2,3,4-tetrahydropyridazin-1- or 2- or 3- or 4- or 5-or 6-yl; 1,2,3,6-tetrahydropyridazin-1- or 2- or 3- or 4- or 5- or 6-yl;1,4,5,6-tetrahydropyridazin-1- or 3- or 4- or 5- or 6-yl;3,4,5,6-tetrahydropyridazin-3- or 4- or 5-yl; 4,5-dihydropyridazin-3- or4-yl; 3,4-dihydropyridazin-3- or 4- or 5- or 6-yl;3,6-dihydropyridazin-3- or 4-yl; 1,6-dihydropyriazin-1- or 3- or 4- or5- or 6-yl; hexahydropyrimidin-1- or 2- or 3- or 4-yl;1,4,5,6-tetrahydropyrimidin-1- or 2- or 4- or 5- or 6-yl;1,2,5,6-tetrahydropyrimidin-1- or 2- or 4- or 5- or 6-yl;1,2,3,4-tetrahydropyrimidin-1- or 2- or 3- or 4- or 5- or 6-yl;1,6-dihydropyrimidin-1- or 2- or 4- or 5- or 6-yl;1,2-dihydropyrimidin-1- or 2- or 4- or 5- or 6-yl;2,5-dihydropyrimidin-2- or 4- or 5-yl; 4,5-dihydropyrimidin-4- or 5- or6-yl; 1,4-dihydropyrimidin-1- or 2- or 4- or 5- or 6-yl; 1- or 2- or3-piperazinyl; 1,2,3,6-tetrahydropyrazin-1- or 2- or 3- or 5- or 6-yl;1,2,3,4-tetrahydropyrazin-1- or 2- or 3- or 4- or 5- or 6-yl;1,2-dihydropyrazin-1- or 2- or 3- or 5- or 6-yl; 1,4-dihydropyrazin-1-or 2- or 3-yl; 2,3-dihydropyrazin-2- or 3- or 5- or 6-yl;2,5-dihydropyrazin-2- or 3-yl; 1,3-dioxolan-2- or 4- or 5-yl;1,3-dioxol-2- or 4-yl; 1,3-dioxan-2- or 4- or 5-yl; 4H-1,3-dioxin-2- or4- or 5- or 6-yl; 1,4-dioxan-2- or 3- or 5- or 6-yl;2,3-dihydro-1,4-dioxin-2- or 3- or 5- or 6-yl; 1,4-dioxin-2- or 3-yl;1,2-dithiolan-3- or 4-yl; 3H-1,2-dithiol-3- or 4- or 5-yl;1,3-dithiolan-2- or 4-yl; 1,3-dithiol-2- or 4-yl; 1,2-dithian-3- or4-yl; 3,4-dihydro-1,2-dithiin-3- or 4- or 5- or 6-yl;3,6-dihydro-1,2-dithiin-3- or 4-yl; 1,2-dithiin-3- or 4-yl;1,3-dithian-2- or 4- or 5-yl; 4H-1,3-dithiin-2- or 4- or 5- or 6-yl;isoxazolidin-2- or 3- or 4- or 5-yl; 2,3-dihydroisoxazol-2- or 3- or 4-or 5-yl; 2,5-dihydroisoxazol-2- or 3- or 4- or 5-yl;4,5-dihydroisoxazol-3- or 4- or 5-yl; 1,3-oxazolidin-2- or 3- or 4- or5-yl; 2,3-dihydro-1,3-oxazol-2- or 3- or 4- or 5-yl;2,5-dihydro-1,3-oxazol-2- or 4- or 5-yl; 4,5-dihydro-1,3-oxazol-2- or 4-or 5-yl; 1,2-oxazinan-2- or 3- or 4- or 5- or 6-yl;3,4-dihydro-2H-1,2-oxazin-2- or 3- or 4- or 5- or 6-yl;3,6-dihydro-2H-1,2-oxazin-2- or 3- or 4- or 5- or 6-yl;5,6-dihydro-2H-1,2-oxazin-2- or 3- or 4- or 5- or 6-yl;5,6-dihydro-4H-1,2-oxazin-3- or 4- or 5- or 6-yl; 2H-1,2-oxazin-2- or 3-or 4- or 5- or 6-yl; 6H-1,2-oxazin-3- or 4- or 5- or 6-yl;4H-1,2-oxazin-3- or 4- or 5- or 6-yl; 1,3-oxazinan-2- or 3- or 4- or 5-or 6-yl; 3,4-dihydro-2H-1,3-oxazin-2- or 3- or 4- or 5- or 6-yl;3,6-dihydro-2H-1,3-oxazin-2- or 3- or 4- or 5- or 6-yl;5,6-dihydro-2H-1,3-oxazin-2- or 4- or 5- or 6-yl;5,6-dihydro-4H-1,3-oxazin-2- or 4- or 5- or 6-yl; 2H-1,3-oxazin-2- or 4-or 5- or 6-yl; 6H-1,3-oxazin-2- or 4- or 5- or 6-yl; 4H-1,3-oxazin-2- or4- or 5- or 6-yl; morpholin-2- or 3- or 4-yl;3,4-dihydro-2H-1,4-oxazin-2- or 3- or 4- or 5- or 6-yl;3,6-dihydro-2H-1,4-oxazin-2- or 3- or 5- or 6-yl; 2H-1,4-oxazin-2- or 3-or 5- or 6-yl; 4H-1,4-oxazin-2- or 3-yl; 1,2-oxazepan-2- or 3- or 4- or5- or 6- or 7-yl; 2,3,4,5-tetrahydro-1,2-oxazepin-2- or 3- or 4- or 5-or 6- or 7-yl; 2,3,4,7-tetrahydro-1,2-oxazepin-2- or 3- or 4- or 5- or6- or 7-yl; 2,3,6,7-tetrahydro-1,2-oxazepin-2- or 3- or 4- or 5- or 6-or 7-yl; 2,5,6,7-tetrahydro-1,2-oxazepin-2- or 3- or 4- or 5- or 6- or7-yl; 4,5,6,7-tetrahydro-1,2-oxazepin-3- or 4- or 5- or 6- or 7-yl;2,3-dihydro-1,2-oxazepin-2- or 3- or 4- or or 6- or 7-yl;2,5-dihydro-1,2-oxazepin-2- or 3- or 4- or 5- or 6- or 7-yl;2,7-dihydro-1,2-oxazepin-2- or 3- or 4- or 5- or 6- or 7-yl;4,5-dihydro-1,2-oxazepin-3- or 4- or 5- or 6- or 7-yl;4,7-dihydro-1,2-oxazepin-3- or 4- or 5- or 6- or 7-yl;6,7-dihydro-1,2-oxazepin-3- or 4- or 5- or 6- or 7-yl; 1,2-oxazepin-3-or 4- or 5- or 6- or 7-yl; 1,3-oxazepan-2- or 3- or 4- or 5- or 6- or7-yl; 2,3,4,5-tetrahydro-1,3-oxazepin-2- or 3- or 4- or 5- or 6- or7-yl; 2,3,4,7-tetrahydro-1,3-oxazepin-2- or 3- or 4- or 5- or 6- or7-yl; 2,3,6,7-tetrahydro-1,3-oxazepin-2- or 3- or 4- or 5- or 6- or7-yl; 2,5,6,7-tetrahydro-1,3-oxazepin-2- or 4- or 5- or 6- or 7-yl;4,5,6,7-tetrahydro-1,3-oxazepin-2- or 4- or 5- or 6- or 7-yl;2,3-dihydro-1,3-oxazepin-2- or 3- or 4- or 5- or 6- or 7-yl;2,5-dihydro-1,3-oxazepin-2- or 4- or 5- or 6- or 7-yl;2,7-dihydro-1,3-oxazepin-2- or 4- or 5- or 6- or 7-yl;4,5-dihydro-1,3-oxazepin-2- or 4- or 5- or 6- or 7-yl;4,7-dihydro-1,3-oxazepin-2- or 4- or 5- or 6- or 7-yl;6,7-dihydro-1,3-oxazepin-2- or 4- or 5- or 6- or 7-yl; 1,3-oxazepin-2-or 4- or or 6- or 7-yl; 1,4-oxazepan-2- or 3- or 5- or 6- or 7-yl;2,3,4,5-tetrahydro-1,4-oxazepin-2- or 3- or 4- or or 6- or 7-yl;2,3,4,7-tetrahydro-1,4-oxazepin-2- or 3- or 4- or 5- or 6- or 7-yl;2,3,6,7-tetrahydro-1,4-oxazepin-2- or 3- or 5- or 6- or 7-yl;2,5,6,7-tetrahydro-1,4-oxazepin-2- or 3- or 5- or 6- or 7-yl;4,5,6,7-tetrahydro-1,4-oxazepin-2- or 3- or 4- or 5- or 6- or 7-yl;2,3-dihydro-1,4-oxazepin-2- or 3- or 5- or 6- or 7-yl;2,5-dihydro-1,4-oxazepin-2- or 3- or 5- or 6- or 7-yl;2,7-dihydro-1,4-oxazepin-2- or 3- or 5- or 6- or 7-yl;4,5-dihydro-1,4-oxazepin-2- or 3- or 4- or 5- or 6- or 7-yl;4,7-dihydro-1,4-oxazepin-2- or 3- or 4- or 5- or 6- or 7-yl;6,7-dihydro-1,4-oxazepin-2- or 3- or 5- or 6- or 7-yl; 1,4-oxazepin-2-or 3- or 5- or 6- or 7-yl; isothiazolidin-2- or 3- or 4- or 5-yl;2,3-dihydroisothiazol-2- or 3- or 4- or 5-yl; 2,5-dihydroisothiazol-2-or 3- or 4- or 5-yl; 4,5-dihydroisothiazol-3- or 4- or 5-yl;1,3-thiazolidin-2- or 3- or 4- or 5-yl; 2,3-dihydro-1,3-thiazol-2- or 3-or 4- or 5-yl; 2,5-dihydro-1,3-thiazol-2- or 4- or 5-yl;4,5-dihydro-1,3-thiazol-2- or 4- or 5-yl; 1,3-thiazinan-2- or 3- or 4-or 5- or 6-yl; 3,4-dihydro-2H-1,3-thiazin-2- or 3- or 4- or 5- or 6-yl;3,6-dihydro-2H-1,3-thiazin-2- or 3- or 4- or 5- or 6-yl;5,6-dihydro-2H-1,3-thiazin-2- or 4- or 5- or 6-yl;5,6-dihydro-4H-1,3-thiazin-2- or 4- or 5- or 6-yl; 2H-1,3-thiazin-2- or4- or or 6-yl; 6H-1,3-thiazin-2- or 4- or 5- or 6-yl; 4H-1,3-thiazin-2-or 4- or 5- or 6-yl. Further examples of “heterocyclyl” are a partly orfully hydrogenated heterocyclic radical having 3 heteroatoms from thegroup of N, O and S, for example 1,4,2-dioxazolidin-2- or 3- or 5-yl;1,4,2-dioxazol-3- or 5-yl; 1,4,2-dioxazinan-2- or -3- or 5- or 6-yl;5,6-dihydro-1,4,2-dioxazin-3- or 5- or 6-yl; 1,4,2-dioxazin-3- or 5- or6-yl; 1,4,2-dioxazepan-2- or 3- or 5- or 6- or 7-yl;6,7-dihydro-5H-1,4,2-dioxazepin-3- or 5- or 6- or 7-yl;2,3-dihydro-7H-1,4,2-dioxazepin-2- or 3- or 5- or 6- or 7-yl;2,3-dihydro-5H-1,4,2-dioxazepin-2- or 3- or 5- or 6- or 7-yl;5H-1,4,2-dioxazepin-3- or 5- or 6- or 7-yl; 7H-1,4,2-dioxazepin-3- or 5-or 6- or 7-yl. Structural examples of heterocycles which are optionallysubstituted further are also listed below:

The heterocycles listed above are preferably substituted, for example,by hydrogen, halogen, alkyl, haloalkyl, hydroxyl, alkoxy, cycloalkoxy,aryloxy, alkoxyalkyl, alkoxyalkoxy, cycloalkyl, halocycloalkyl, aryl,arylalkyl, heteroaryl, heterocyclyl, alkenyl, alkylcarbonyl,cycloalkylcarbonyl, arylcarbonyl, heteroarylcarbonyl, alkoxycarbonyl,hydroxycarbonyl, cycloalkoxycarbonyl, cycloalkylalkoxycarbonyl,alkoxycarbonylalkyl, arylalkoxycarbonyl, arylalkoxycarbonylalkyl,alkynyl, alkynylalkyl, alkylalkynyl, trisalkylsilylalkynyl, nitro,amino, cyano, haloalkoxy, haloalkylthio, alkylthio, hydrothio,hydroxyalkyl, oxo, heteroarylalkoxy, arylalkoxy, heterocyclylalkoxy,heterocyclylalkylthio, heterocyclyloxy, heterocyclylthio, heteroaryloxy,bisalkylamino, alkylamino, cycloalkylamino, hydroxycarbonylalkylamino,alkoxycarbonylalkylamino, arylalkoxycarbonylalkylamino,alkoxycarbonylalkyl(alkyl)amino, aminocarbonyl, alkylaminocarbonyl,bisalkylaminocarbonyl, cycloalkylaminocarbonyl,hydroxycarbonylalkylaminocarbonyl, alkoxycarbonylalkylaminocarbonyl,arylalkoxycarbonylalkylaminocarbonyl.

When a base structure is substituted “by one or more radicals” from alist of radicals (=group) or a generically defined group of radicals,this in each case includes simultaneous substitution by a plurality ofidentical and/or structurally different radicals.

In the case of a partly or fully saturated nitrogen heterocycle, thismay be joined to the remainder of the molecule either via carbon or viathe nitrogen.

Suitable substituents for a substituted heterocyclic radical are thesubstituents specified further down, and additionally also oxo andthioxo. The oxo group as a substituent on a ring carbon atom is then,for example, a carbonyl group in the heterocyclic ring. As a result,lactones and lactams are preferably also included.

The oxo group may also occur on the ring heteroatoms, which may exist indifferent oxidation states, for example in the case of N and S, and inthat case form, for example, the divalent —N(O)—, —S(O)— (also SO forshort) and —S(O)₂— (also SO 2 for short) groups in the heterocyclicring. In the case of —N(O)— and —S(O)— groups, both enantiomers in eachcase are included.

According to the invention, the expression “heteroaryl” representsheteroaromatic compounds, i.e. fully unsaturated aromatic heterocycliccompounds, preferably 5- to 7-membered rings having 1 to 4, preferably 1or 2, identical or different heteroatoms, preferably O, S or N.Inventive heteroaryls are, for example, 1H-pyrrol-1-yl; 1H-pyrrol-2-yl;1H-pyrrol-3-yl; furan-2-yl; furan-3-yl; thien-2-yl; thien-3-yl,1H-imidazol-1-yl; 1H-imidazol-2-yl; 1H-imidazol-4-yl; 1H-imidazol-5-yl;1H-pyrazol-1-yl; 1H-pyrazol-3-yl; 1H-pyrazol-4-yl; 1H-pyrazol-5-yl,1H-1,2,3-triazol-1-yl, 1H-1,2,3-triazol-4-yl, 1H-1,2,3-triazol-5-yl,2H-1,2,3-triazol-2-yl, 2H-1,2,3-triazol-4-yl, 1H-1,2,4-triazol-1-yl,1H-1,2,4-triazol-3-yl, 4H-1,2,4-triazol-4-yl, 1,2,4-oxadiazol-3-yl,1,2,4-oxadiazol-5-yl, 1,3,4-oxadiazol-2-yl, 1,2,3-oxadiazol-4-yl,1,2,3-oxadiazol-5-yl, 1,2,5-oxadiazol-3-yl, azepinyl, pyridin-2-yl,pyridin-3-yl, pyridin-4-yl, pyrazin-2-yl, pyrazin-3-yl, pyrimidin-2-yl,pyrimidin-4-yl, pyrimidin-5-yl, pyridazin-3-yl, pyridazin-4-yl,1,3,5-triazin-2-yl, 1,2,4-triazin-3-yl, 1,2,4-triazin-5-yl,1,2,4-triazin-6-yl, 1,2,3-triazin-4-yl, 1,2,3-triazin-5-yl, 1,2,4-,1,3,2-, 1,3,6- and 1,2,6-oxazinyl, isoxazol-3-yl, isoxazol-4-yl,isoxazol-5-yl, 1,3-oxazol-2-yl, 1,3-oxazol-4-yl, 1,3-oxazol-5-yl,isothiazol-3-yl, isothiazol-4-yl, isothiazol-5-yl, 1,3-thiazol-2-yl,1,3-thiazol-4-yl, 1,3-thiazol-5-yl, 1,3,4-thiadiazol-2-yl,1,3,4-thiadiazol-5-yl, 1,2,4-thiadiazol-5-yl, 1,2,4-thiadiazol-3-yl,1,2,5-thiadiazol-3-yl, 1,2,5-thiadiazol-3-yl, 1,2,3-thiadiazol-4-yl,1,2,3-thiadiazol-5-yl, oxepinyl, thiepinyl, 1,2,4-triazolonyl and1,2,4-diazepinyl, 2H-1,2,3,4-tetrazol-5-yl, 1H-1,2,3,4-tetrazol-5-yl,1,2,3,4-oxatriazol-5-yl, 1,2,3,4-thiatriazol-5-yl,1,2,3,5-oxatriazol-4-yl, 1,2,3,5-thiatriazol-4-yl. The heteroaryl groupsof the invention may also be substituted by one or more identical ordifferent radicals.

If two adjacent carbon atoms are part of a further aromatic ring, thesystems are fused heteroaromatic systems, such as benzofused orpolyannelated heteroaromatics. Preferred examples are quinolines (e.g.quinolin-2-yl, quinolin-3-yl, quinolin-4-yl, quinolin-5-yl,quinolin-6-yl, quinolin-7-yl, quinolin-8-yl); isoquinolines (e.g.isoquinolin-1-yl, isoquinolin-3-yl, isoquinolin-4-yl, isoquinolin-5-yl,isoquinolin-6-yl, isoquinolin-7-yl, isoquinolin-8-yl); quinoxaline;quinazoline; cinnoline; 1,5-naphthyridine; 1,6-naphthyridine;1,7-naphthyridine; 1,8-naphthyridine; 2,6-naphthyridine;2,7-naphthyridine; phthalazine; pyridopyrazines; pyridopyrimidines;pyridopyridazines; pteridines; pyrimidopyrimidines. Examples ofheteroaryl are also 5- or 6-membered benzofused rings from the group of1H-indol-1-yl, 1H-indol-2-yl, 1H-indol-3-yl, 1H-indol-4-yl,1H-indol-5-yl, 1H-indol-6-yl, 1H-indol-7-yl, 1-benzofuran-2-yl,1-benzofuran-3-yl, 1-benzofuran-4-yl, 1-benzofuran-5-yl,1-benzofuran-6-yl, 1-benzofuran-7-yl, 1-benzo-thiophen-2-yl,1-benzothiophen-3-yl, 1-benzothiophen-4-yl, 1-benzothiophen-5-yl,1-benzothiophen-6-yl, 1-benzothiophen-7-yl, 1H-indazol-1-yl,1H-indazol-3-yl, 1H-indazol-4-yl, 1H-indazol-5-yl, 1H-indazol-6-yl,1H-indazol-7-yl, 2H-indazol-2-yl, 2H-indazol-3-yl, 2H-indazol-4-yl,2H-indazol-5-yl, 2H-indazol-6-yl, 2H-indazol-7-yl, 2H-isoindol-2-yl,2H-isoindol-1-yl, 2H-isoindol-3-yl, 2H-isoindol-4-yl, 2H-isoindol-5-yl,2H-isoindol-6-yl; 2H-isoindol-7-yl, 1H-benzimidazol-1-yl,1H-benzimidazol-2-yl, 1H-benzimidazol-4-yl, 1H-benzimidazol-5-yl,1H-benzimidazol-6-yl, 1H-benzimidazol-7-yl, 1,3-benzoxazol-2-yl,1,3-benzoxazol-4-yl, 1,3-benzoxazol-5-yl, 1,3-benzoxazol-6-yl,1,3-benzoxazol-7-yl, 1,3-benzothiazol-2-yl, 1,3-benzothiazol-4-yl,1,3-benzothiazol-5-yl, 1,3-benzothiazol-6-yl, 1,3-benzothiazol-7-yl,1,2-benzisoxazol-3-yl, 1,2-benzisoxazol-4-yl, 1,2-benzisoxazol-5-yl,1,2-benzisoxazol-6-yl, 1,2-benzisoxazol-7-yl, 1,2-benzisothiazol-3-yl,1,2-benzisothiazol-4-yl, 1,2-benzisothiazol-5-yl,1,2-benzisothiazol-6-yl, 1,2-benzisothiazol-7-yl.

The term “halogen” denotes, for example, fluorine, chlorine, bromine oriodine. If the term is used for a radical, “halogen” denotes, forexample, a fluorine, chlorine, bromine or iodine atom.

According to the invention, “alkyl” means a straight-chain or branchedopen-chain, saturated hydrocarbon radical which is optionally mono- orpolysubstituted, and in the latter case is referred to as “substitutedalkyl”. Preferred substituents are halogen atoms, alkoxy, haloalkoxy,cyano, alkylthio, haloalkylthio, cycloalkyl, alkoxycarbonyl,hydroxycarbonyl, heterocyclyl, hetaryl, aryl, amino or nitro groups,particular preference being given to methoxy, methyl, fluoroalkyl,cyano, nitro, fluorine, chlorine, bromine or iodine. The prefix “bis”also includes the combination of different alkyl radicals, e.g.methyl(ethyl) or ethyl(methyl).

“Haloalkyl”, “-alkenyl” and “-alkynyl” respectively denote alkyl,alkenyl and alkynyl partly or fully substituted by identical ordifferent halogen atoms, for example monohaloalkyl such as CH₂CH₂Cl,CH₂CH₂Br, CHClCH₃, CH₂Cl, CH₂F; perhaloalkyl such as CCl₃, CClF₂, CFCl₂,CF₂CClF₂, CF₂CClFCF₃; polyhaloalkyl such as CH₂CHFCl, CF₂CClFH,CF₂CBrFH, CH₂CF₃; the term perhaloalkyl also encompasses the termperfluoroalkyl.

“Partially fluorinated alkyl” denotes a straight-chain or branched,saturated hydrocarbon which is mono- or polysubstituted by fluorine,where the fluorine atoms in question may be present as substituents onone or more different carbon atoms of the straight-chain or branchedhydrocarbon chain, for example CHFCH₃, CH₂CH₂F, CH₂CH₂CF₃, CHF₂, CH₂F,CHFCF₂CF₃.

“Partly fluorinated haloalkyl” denotes a straight-chain or branched,saturated hydrocarbon which is substituted by different halogen atomswith at least one fluorine atom, where any other halogen atomsoptionally present are selected from the group consisting of fluorine,chlorine or bromine, iodine. The corresponding halogen atoms may bepresent as substituents on one or more different carbon atoms of thestraight-chain or branched hydrocarbon chain. Partly fluorinatedhaloalkyl also includes full substitution of the straight or branchedchain by halogen including at least one fluorine atom.

“Haloalkoxy” is, for example, OCF₃, OCHF₂, OCH₂F, OCF₂CF₃, OCH₂CF₃ andOCH₂CH₂Cl; this applies correspondingly to haloalkenyl and otherhalogen-substituted radicals.

The expression “(C₁-C₄)-alkyl” mentioned here by way of example is abrief notation for straight-chain or branched alkyl having one to 4carbon atoms according to the range stated for carbon atoms, i.e.encompasses the methyl, ethyl, 1-propyl, 2-propyl, 1-butyl, 2-butyl,2-methylpropyl or tert-butyl radicals. General alkyl radicals with alarger specified range of carbon atoms, e.g. “(C₁-C₆)-alkyl”,correspondingly also encompass straight-chain or branched alkyl radicalswith a greater number of carbon atoms, i.e. according to the examplealso the alkyl radicals having 5 and 6 carbon atoms.

Unless stated specifically, preference is given to the lower carbonskeletons, for example having from 1 to 6 carbon atoms, or having from 2to 6 carbon atoms in the case of unsaturated groups, in the case of thehydrocarbon radicals such as alkyl, alkenyl and alkynyl radicals,including in composite radicals. Alkyl radicals, including in compositeradicals such as alkoxy, haloalkyl, etc., are, for example, methyl,ethyl, n-propyl or i-propyl, n-, t- or 2-butyl, pentyls, hexyls such asn-hexyl, i-hexyl and 1,3-dimethylbutyl, heptyls such as n-heptyl,1-methylhexyl and 1,4-dimethylpentyl; alkenyl and alkynyl radicals aredefined as the possible unsaturated radicals corresponding to the alkylradicals, where at least one double bond or triple bond is present.Preference is given to radicals having one double bond or triple bond.

The term “alkenyl” also includes, in particular, straight-chain orbranched open-chain hydrocarbon radicals having more than one doublebond, such as 1,3-butadienyl and 1,4-pentadienyl, but also allenyl orcumulenyl radicals having one or more cumulated double bonds, forexample allenyl (1,2-propadienyl), 1,2-butadienyl and1,2,3-pentatrienyl. Alkenyl denotes, for example, vinyl which mayoptionally be substituted by further alkyl radicals, for example (butnot limited thereto) (C₂-C₆)-alkenyl such as ethenyl, 1-propenyl,2-propenyl, 1-methylethenyl, 1-butenyl, 2-butenyl, 3-butenyl,1-methyl-1-propenyl, 2-methyl-1-propenyl, 1-methyl-2-propenyl,2-methyl-2-propenyl, 1-pentenyl, 2-pentenyl, 3-pentenyl, 4-pentenyl,1-methyl-1-butenyl, 2-methyl-1-butenyl, 3-methyl-1-butenyl,1-methyl-2-butenyl, 2-methyl-2-butenyl, 3-methyl-2-butenyl,1-methyl-3-butenyl, 2-methyl-3-butenyl, 3-methyl-3-butenyl,1,1-dimethyl-2-propenyl, 1,2-dimethyl-1-propenyl,1,2-dimethyl-2-propenyl, 1-ethyl-1-propenyl, 1-ethyl-2-propenyl,1-hexenyl, 2-hexenyl, 3-hexenyl, 4-hexenyl, 5-hexenyl,1-methyl-1-pentenyl, 2-methyl-1-pentenyl, 3-methyl-1-pentenyl,4-methyl-1-pentenyl, 1-methyl-2-pentenyl, 2-methyl-2-pentenyl,3-methyl-2-pentenyl, 4-methyl-2-pentenyl, 1-methyl-3-pentenyl,2-methyl-3-pentenyl, 3-methyl-3-pentenyl, 4-methyl-3-pentenyl,1-methyl-4-pentenyl, 2-methyl-4-pentenyl, 3-methyl-4-pentenyl,4-methyl-4-pentenyl, 1,1-dimethyl-2-butenyl, 1,1-dimethyl-3-butenyl,1,2-dimethyl-1-butenyl, 1,2-dimethyl-2-butenyl, 1,2-dimethyl-3-butenyl,1,3-dimethyl-1-butenyl, 1,3-dimethyl-2-butenyl, 1,3-dimethyl-3-butenyl,2,2-dimethyl-3-butenyl, 2,3-dimethyl-1-butenyl, 2,3-dimethyl-2-butenyl,2,3-dimethyl-3-butenyl, 3,3-dimethyl-1-butenyl, 3,3-dimethyl-2-butenyl,1-ethyl-1-butenyl, 1-ethyl-2-butenyl, 1-ethyl-3-butenyl,2-ethyl-1-butenyl, 2-ethyl-2-butenyl, 2-ethyl-3-butenyl,1,1,2-trimethyl-2-propenyl, 1-ethyl-1-methyl-2-propenyl,1-ethyl-2-methyl-1-propenyl and 1-ethyl-2-methyl-2-propenyl.

The term “alkynyl” also includes, in particular, straight-chain orbranched open-chain hydrocarbon radicals having more than one triplebond, or else having one or more triple bonds and one or more doublebonds, for example 1,3-butatrienyl or 3-penten-1-yn-1-yl.(C₂-C₆)-Alkynyl denotes, for example, ethynyl, 1-propynyl, 2-propynyl,1-butynyl, 2-butynyl, 3-butynyl, 1-methyl-2-propynyl, 1-pentynyl,2-pentynyl, 3-pentynyl, 4-pentynyl, 1-methyl-2-butynyl,1-methyl-3-butynyl, 2-methyl-3-butynyl, 3-methyl-1-butynyl,1,1-dimethyl-2-propynyl, 1-ethyl-2-propynyl, 1-hexynyl, 2-hexynyl,3-hexynyl, 4-hexynyl, 5-hexynyl, 1-methyl-2-pentynyl,1-methyl-3-pentynyl, 1-methyl-4-pentynyl, 2-methyl-3-pentynyl,2-methyl-4-pentynyl, 3-methyl-1-pentynyl, 3-methyl-4-pentynyl,4-methyl-1-pentynyl, 4-methyl-2-pentynyl, 1,1-dimethyl-2-butynyl,1,1-dimethyl-3-butynyl, 1,2-dimethyl-3-butynyl, 2,2-dimethyl-3-butynyl,3,3-dimethyl-1-butynyl, 1-ethyl-2-butynyl, 1-ethyl-3-butynyl,2-ethyl-3-butynyl and 1-ethyl-1-methyl-2-propynyl.

The term “cycloalkyl” refers to a carbocyclic saturated ring systemhaving preferably 3-8 ring carbon atoms, for example cyclopropyl,cyclobutyl, cyclopentyl or cyclohexyl, which optionally has furthersubstitution, preferably by hydrogen, alkyl, alkoxy, cyano, nitro,alkylthio, haloalkylthio, halogen, alkenyl, alkynyl, haloalkyl, amino,alkylamino, bisalkylamino, alkoxycarbonyl, hydroxycarbonyl,arylalkoxycarbonyl, aminocarbonyl, alkylaminocarbonyl,cycloalkylaminocarbonyl. In the case of optionally substitutedcycloalkyl, cyclic systems with substituents are included, alsoincluding substituents with a double bond on the cycloalkyl radical, forexample an alkylidene group such as methylidene. In the case ofoptionally substituted cycloalkyl, polycyclic aliphatic systems are alsoincluded, for example bicyclo[1.1.0]butan-1-yl,bicyclo[1.1.0]butan-2-yl, bicyclo[2.1.0]pentan-1-yl,bicyclo[1.1.1]pentan-1-yl, bicyclo[2.1.0]pentan-2-yl,bicyclo[2.1.0]pentan-5-yl, bicyclo[2.1.1]hexyl, bicyclo[2.2.1]hept-2-yl,bicyclo[2.2.2]octan-2-yl, bicyclo[3.2.1]octan-2-yl,bicyclo[3.2.2]nonan-2-yl, adamantan-1-yl and adamantan-2-yl, but alsosystems such as 1,1′-bi(cyclopropyl)-1-yl, 1,1′-bi(cyclopropyl)-2-yl,for example. The term “(C₃-C₇)-cycloalkyl” is a brief notation forcycloalkyl having three to 7 carbon atoms, corresponding to the rangespecified for carbon atoms.

In the case of substituted cycloalkyl, spirocyclic aliphatic systems arealso included, for example spiro[2.2]pent-1-yl, spiro[2.3]hex-1-yl,spiro[2.3]hex-4-yl, 3-spiro[2.3]hex-5-yl, spiro[3.3]hept-1-yl,spiro[3.3]hept-2-yl.

“Cycloalkenyl” denotes a carbocyclic, nonaromatic, partly unsaturatedring system having preferably 4-8 carbon atoms, e.g. 1-cyclobutenyl,2-cyclobutenyl, 1-cyclopentenyl, 2-cyclopentenyl, 3-cyclopentenyl, or1-cyclohexenyl, 2-cyclohexenyl, 3-cyclohexenyl, 1,3-cyclohexadienyl or1,4-cyclohexadienyl, also including substituents with a double bond onthe cycloalkenyl radical, for example an alkylidene group such asmethylidene. In the case of optionally substituted cycloalkenyl, theelucidations for substituted cycloalkyl apply correspondingly.

The term “alkylidene”, also, for example, in the form(C₁-C₁₀)-alkylidene, denotes the radical of a straight-chain or branchedopen-chain hydrocarbon radical which is attached via a double bond.Possible bonding sites for alkylidene are naturally only positions onthe base structure where two hydrogen atoms can be replaced by thedouble bond; radicals are, for example, ═CH₂, ═CH—CH₃, ═C(CH₃)—CH₃,═C(CH₃)—C₂H₅ or ═C(C₂H₅)—C₂H₅. Cycloalkylidene denotes a carbocyclicradical bonded via a double bond.

“Alkoxyalkyl” represents an alkoxy radical bonded via an alkyl group and“alkoxyalkoxy” denotes an alkoxyalkyl radical bonded via an oxygen atom,for example (but not limited to) methoxymethoxy, methoxyethoxy,ethoxyethoxy, methoxy-n-propyloxy.

“Arylalkyl” represents an aryl radical bonded via an alkyl group,“heteroarylalkyl” denotes a heteroaryl radical bonded via an alkylgroup, and “heterocyclylalkyl” denotes a heterocyclyl radical bonded viaan alkyl group.

“Cycloalkylalkyl” represents a cycloalkyl radical bonded via an alkylgroup, for example (but not limited thereto) cyclopropylmethyl,cyclobutylmethyl, cyclopentylmethyl, cyclohexylmethyl,1-cyclopropyleth-1-yl, 2-cyclopropyleth-1-yl, 1-cyclopropylprop-1-yl,3-cyclopropylprop-1-yl.

According to the invention, “haloalkylthio”—on its own or as constituentpart of a chemical group—is straight-chain or branched S-haloalkyl,preferably having 1 to 8, or having 1 to 6 carbon atoms, such as(C₁-C₈)—, (C₁-C₆)- or (C₁-C₄)-haloalkylthio, for example (but notlimited to) trifluoromethylthio, pentafluoroethylthio, difluoromethyl,2,2-difluoroeth-1-ylthio, 2,2,2-difluoroeth-1-ylthio,3,3,3-prop-1-ylthio.

“Halocycloalkyl” denotes cycloalkyl or cycloalkenyl partly or fullysubstituted by identical or different halogen atoms, such as F, Cl andBr, or by haloalkyl, such as trifluoromethyl or difluoromethyl, forexample 1-fluorocycloprop-1-yl, 2-fluorocycloprop-1-yl,2,2-difluorocycloprop-1-yl, 1-fluorocyclobut-1-yl,1-trifluoromethylcycloprop-1-yl, 2-trifluoromethylcycloprop-1-yl,1-chlorocycloprop-1-yl, 2-chlorocycloprop-1-yl,2,2-dichlorocycloprop-1-yl, 3,3-difluorocyclobutyl.

If the compounds can form, through a hydrogen shift, tautomers whosestructure would not formally be covered by the general formula (I),these tautomers are nevertheless encompassed by the definition of theinventive compounds of the general formula (I), unless a particulartautomer is under consideration. For example, many carbonyl compoundsmay be present both in the keto form and in the enol form, both formsbeing encompassed by the definition of the compound of the generalformula (I).

Depending on the nature of the substituents and the manner in which theyare attached, the compounds of the general formula (I) may be present asstereoisomers. The possible stereoisomers defined by the specificthree-dimensional form thereof, such as enantiomers, diastereomers, Zand E isomers, are all encompassed by the general formula (I). If, forexample, one or more alkenyl groups are present, diastereomers (Z and Eisomers) may occur. If, for example, one or more asymmetric carbon atomsare present, enantiomers and diastereomers may occur. Stereoisomers canbe obtained from the mixtures obtained in the preparation by customaryseparation methods. The chromatographic separation can be effectedeither on the analytical scale to find the enantiomeric excess or thediastereomeric excess, or else on the preparative scale to produce testspecimens for biological testing. It is likewise possible to selectivelyprepare stereoisomers by using stereoselective reactions with use ofoptically active starting materials and/or auxiliaries. The inventionthus also relates to all stereoisomers which are embraced by the generalformula (I) but are not shown in their specific stereomeric form, and tomixtures thereof.

If the compounds are obtained as solids, the purification can also becarried out by recrystallization or digestion. If individual compounds(I) cannot be obtained in a satisfactory manner by the routes describedbelow, they can be prepared by derivatization of other compounds (I).

Suitable isolation methods, purification methods and methods forseparating stereoisomers of compounds of the general formula (I) aremethods generally known to the person skilled in the art from analogouscases, for example by physical processes such as crystallization,chromatographic methods, in particular column chromatography and HPLC(high pressure liquid chromatography), distillation, optionally underreduced pressure, extraction and other methods, any mixtures that remaincan generally be separated by chromatographic separation, for example onchiral solid phases. Suitable for preparative amounts or on anindustrial scale are processes such as crystallization, for example ofdiastereomeric salts which can be obtained from the diastereomermixtures using optically active acids and, if appropriate, provided thatacidic groups are present, using optically active bases.

Synthesis of [(5-phenyl-1-(heteroaryl)-1H-1,2,4-triazol-3-yl)oxy]aceticacid derivatives of the general formula (I)

The inventive [(5-phenyl-1-(hetero aryl)-1H-1,2,4-triazol-3-yl)oxy]acetic acid derivatives of the general formula (I) can be preparedproceeding from known processes. The synthesis routes used and examinedproceed from commercially available or readily preparable substitutedbenzoic acids, from correspondingly substituted benzamides and fromcommercially available chemicals, such as substituted heteroarylhydrazines and diphenyl carbonate. In the schemes which follow, themoieties R¹, R², R³, R⁴, n and p in the general formula (I) have themeanings defined above, unless illustrative but non-limiting definitionsare given.

The inventive compounds of the general formula (Ia) are synthesized viaa reaction of the compound of the general formula (II) with a compoundof the general formula (III) in the presence of a base, for examplepotassium carbonate. The reaction preferably takes place in thetemperature range between 0° C. and 120° C., in a suitable solvent, forexample acetonitrile (see scheme 1).

The compounds of the general formula (II) are synthesized via acyclization of a compound of the general formula (IV) in the presence ofa condensation reagent, for example polyphosphoric acid. The reactionpreferably takes place within the temperature range between 0° C. and180° C., in neat form (see scheme 2).

The synthesis of compounds of the general formula (IV) can be preparedby reaction of the compound of the general formula (V) with aphenylhydrazine of the general formula (VI) in a suitable solvent, forexample acetonitrile, within a temperature range between −20° C. and100° C., preferably −5° C. and 50° C. The reaction takes place in thepresence of a base, for example triethylamine. Rather thanheteroarylhydrazines of the general formula (VI), it is also possible touse heteroarylhydrazine hydrohalides of the general formula (VII)(scheme 3).

The synthesis of the compound of the general formula (V) can be preparedby reaction of the compound of the general formula (VIII) with diphenylcarbonate (IX) in the presence of a base, for example sodium hydride(see Scheme 4). The reaction preferably takes place in the temperaturerange between −20° C. and 150° C., in a suitable solvent, for exampleTHF. The compounds of the general formula (VIII) and (IX) arecommercially available or can be prepared analogously to methods knownto the person skilled in the art.

The synthesis of the acid of the general formula (X) can be prepared byhydrolysis of the compound of the general formula (Ia) by or analogouslyto methods known to those skilled in the art.

The hydrolysis can be carried out in the presence of a base or a Lewisacid. The base may be a hydroxide salt of an alkali metal (for examplelithium, sodium or potassium; Scheme 5), and the hydrolysis reactionpreferably takes place in the temperature range between room temperatureand 100° C. The Lewis acid may be boron tribromide, and the reaction canbe carried out within a temperature range between −20° C. and 100° C.,preferably −5° C. and 50° C.

The inventive compounds of the general formula (XI) are synthesized viaan esterification of an acid of the general formula (X) with an alcoholof the general formula (XII) in the presence of a coupling reagent, forexample T3P, dicyclohexylcarbodiimide,N-(3-dimethylaminopropyl)-N′-ethylcarbodiimide,N,N′-carbonyldiimidazole, 2-chloro-1,3-dimethylimidazolium chloride or2-chloro-1-methylpyridinium iodide (see Chemistry of Peptide Synthesis,Ed. N. Leo Benoiton, Taylor & Francis, 2006, ISBN-10: 1-57444-454-9).Polymer-supported reagents, for example polymer-supporteddicyclohexylcarbodiimide, are also suitable for this coupling reaction.The reaction takes place preferably within the temperature range between0° C. and 80° C., in an appropriate solvent, for exampledichloromethane, acetonitrile, N,N-dimethylformamide or ethyl acetate,and in the presence of a base, for example triethylamine,N,N-diisopropylethylamine or 1,8-diazabicyclo[5.4.0]undec-7-ene (seeScheme 6). For T3P coupling conditions see Organic Process Research &Development 2009, 13, 900-906.

Scheme 7 shows the synthesis of the compound of the general formula(II); the synthesis is effected by reaction of a compound of the generalformula (XIII) in the presence of a Brønsted acid, for example 33% HBrin acetic acid. The reaction preferably takes place in the temperaturerange between 0° C. and 180° C. See Bioorganic & Medicinal Chemistry2018, 26, 3321-3344.

Compounds of the general formula (XIII) can be prepared by reaction of acompound of the general formula (XIV) and a heteroarylhydrazine of thegeneral formula (VI) in a suitable solvent, for example ethanol (seeScheme 8). The reaction preferably takes place in the temperature rangebetween 0° C. and 150° C.

The compounds of the general formula (XIV) can be prepared by reactionof benzoyl halides of the general formula (XV) with a thiocyanate saltof the general formula (XVI) in the presence of methanol in a suitablesolvent, for example acetone (see Scheme 9). The benzoyl halides areeither commercially available or can be prepared analogously to methodsknown to the person skilled in the art. See Tetrahedron 1968, 24,5205-5214; J. Chem. Soc. 1957, 1091; JP81 53, 664 (1981); Justus LiebigsAnn. Chem. 1964, 675, 180 and J. heterocycl. Chem. 1983, 20, 1533.

Selected detailed synthesis examples for the inventive compounds of thegeneral formula (I) are adduced below. The example numbers mentionedcorrespond to the numbering scheme in Tables I.1 to 1.77 below.

The ¹H NMR, ¹³C-NMR and ¹⁹F-NMR spectroscopy data reported for thechemical examples described in the sections which follow (400 MHz for ¹HNMR and 150 MHz for ¹³C-NMR and 375 MHz for ¹⁹F-NMR, solvent CDCl₃,CD₃OD or d₆-DMSO, internal standard: tetramethylsilane δ=0.00 ppm) wereobtained on a Bruker instrument, and the signals listed have themeanings given below: br=broad; s=singlet, d=doublet, t=triplet,dd=doublet of doublets, ddd=doublet of a doublet of doublets,m=multiplet, q=quartet, quint=quintet, sext=sextet, sept=septet,dq=doublet of quartets, dt=doublet of triplets. In the case ofdiastereomer mixtures, either the significant signals for each of thetwo diastereomers are reported or the characteristic signal of the maindiastereomer is reported. The abbreviations used for chemical groupshave, for example, the following meanings: Me=CH₃, Et=CH₂CH₃,t-Hex=C(CH₃)₂CH(CH₃)₂, t-Bu=C(CH₃) 3, n-Bu=unbranched butyl,n-Pr=unbranched propyl, i-Pr=branched propyl, c-Pr=cyclopropyl,c-Hex=cyclohexyl.

SYNTHESIS EXAMPLES Synthesis Example No.: 1.42-11 Synthesis Stage 1:Phenyl (2,4-difluorobenzoyl)carbamate

2,4-Difluorobenzamide (10 g, 63.65 mmol, 1.0 equiv) and diphenylcarbonate (20.45 g, 1.5 equiv) were dissolved in THF (100 ml) under anargon atmosphere and cooled down to 0° C. with an ice bath. Sodiumhydride (60% in mineral oil, 2.55 g, 63.65 mmol, 1.0 equiv) was added inportions to the solution. Caution: evolution of gas! Subsequently, theice bath is removed and the reaction mixture is stirred at roomtemperature for 1 h. Thereafter, the reaction mixture was concentratedto ⅓ under reduced pressure, forming a flaky white solid. The resultantsolid was filtered off with suction and dried under air. Phenyl(2,4-difluorobenzoyl)carbamate was isolated in the form of a white solid(11.51 g, 61% of theory). ¹H-NMR (400 MHz, DMSO-d⁶ δ, ppm) 7.76 (m, 1H),7.36-7.28 (m, 2H), 7.18-6.99 (m, 4H), 6.77-6.74 (m, 2H).

Synthesis Stage 2:2N-(2,4-Difluorobenzoyl)-2-(5-fluoropyridin-2-yl)hydrazinecarboxamide

Phenyl (2,4-difluorobenzoyl)carbamate (2.5 g, 9.02 mmol, 1.0 equiv) wasdissolved in acetonitrile (100 ml) and then the following were added atroom temperature: 5-fluoro-2-hydrazinopyridine (1.26 g, 9.92 mmol, 1.1equiv) and triethylamine (3.77 ml, 27.05 mmol, 3.0 equiv). The solutionturned pink after about 15-30 min, and a beige solid precipitated out.The reaction mixture was stirred at room temperature for 1 h, then theresultant precipitate was filtered off and dried under air.N-(2,4-Difluorobenzoyl)-2-(5-fluoropyridin-2-yl)hydrazinecarboxamide wasisolated in the form of a beige solid (2.40 g, 42% of theory). ¹H-NMR(400 MHz, DMSO-d⁶ δ, ppm) 11.45 (bs, 1H), 9.63 (bs, 1H), 8.09-8.00 (m,2H), 7.78-7.61 (m, 2H), 7.09-7.02 (m, 2H), 6.85 (d, 1H).

Synthesis Stage 3:5-(2,4-Difluorophenyl)-1-(5-fluoropyridin-2-yl)-1H-1,2,4-triazole-3-ol

2N-(2,4-Difluorobenzoyl)-2-(5-fluoropyridin-2-yl)hydrazinecarboxamide(0.9 g, 2.90 mmol, 1.0 equiv) was blended in polyphosphoric acid (20 g)and then at 100° C. for 2.5 h, liquefying the reaction mixture. Afterhaving been cooled down to room temperature, the reaction mixture wasadded dropwise to ice-water, and the pale beige precipitate was filteredoff with suction. The precipitate was filtered off with suction anddried at 55° C. in a vacuum drying cabinet.5-(2,4-Difluorophenyl)-1-(5-fluoropyridin-2-yl)-1H-1,2,4-triazole-3-olwas isolated in the form of a pale beige solid (180 mg, 20% of theory).¹H-NMR (400 MHz, DMSO-d⁶ δ, ppm) 11.80 (bs, 1H), 8.26 (m, 1H), 7.99 (m,1H), 7.78 (m, 1H), 7.66 (m, 1H), 7.40 (m, 1H), 7.23 (m, 1H).

Synthesis Stage 4: Methyl{[5-(2,4-difluorophenyl)-1-(5-fluoropyridin-2-yl)-1H-1,2,4-triazol-3-yl]oxy}acetate(synthesis example 1.40-9)

5-(2,4-Difluorophenyl)-1-(5-fluoropyridin-2-yl)-1H-1,2,4-triazole-3-ol(161 mg, 0.55 mmol, 1.0 equiv) and potassium carbonate (228 mg, 1.65mmol, 3 equiv) were suspended in acetonitrile (10 ml), and then methylbromoacetate (126 mg, 0.83 mmol, 1.5 equiv) was added. Then thesuspension was stirred at room temperature overnight, the solid wasfiltered off, and the reaction mixture was concentrated under reducedpressure. The residue was purified by column chromatography (ethylacetate/heptane gradient). Methyl{[5-(2,4-difluorophenyl)-1-(5-fluoropyridin-2-yl)-1H-1,2,4-triazol-3-yl]oxy}acetatewas isolated in the form of a colorless oil (152 mg, 71% of theory).¹H-NMR (400 MHz, CDCl₃ δ, ppm) 8.04 (d, 1H), 7.77-7.67 (m, 2H), 7.56 (m,1H), 7.01 (m, 1H), 6.77 (m, 1H), 4.97 (s, 2H), 3.82 (s, 3H).

Synthesis Stage 5:{[5-(2,4-Difluorophenyl)-1-(5-fluoropyridin-2-yl)-1H-1,2,4-triazol-3-yl]oxy}aceticAcid (Synthesis Example 1.42-11)

Methyl{[5-(2,4-difluorophenyl)-1-(5-fluoropyridin-2-yl)-1H-1,2,4-triazol-3-yl]oxy}acetate(90 mg, mmol, 1.0 equiv) and lithium hydroxide (12 mg, 0.49 mmol, 2equiv) were dissolved in a THF/water mixture (7:2, 13 ml) and thenstirred at room temperature for 1 h. The reaction mixture wasconcentrated under reduced pressure. The residue was dissolved in waterand adjusted to pH=2 with 2M hydrochloric acid, with precipitation of apale yellow solid. The precipitate was filtered off with suction anddried at in a vacuum drying cabinet.{[5-(2,4-Difluorophenyl)-1-(5-fluoropyridin-2-yl)-1H-1,2,4-triazol-3-yl]oxy}aceticacid was isolated in the form of a pale yellow solid (85 mg, 93% oftheory). ¹H-NMR (400 MHz, DMSO-d⁶ δ, ppm) 13.18 (bs, 1H), 8.31 (m, 1H),8.01 (m, 1H), 7.79 (m, 1H), 7.71 (m, 1H), 7.37 (m, 1H), 7.25 (m, 1H),4.91 (s, 2H).

In analogy to the preparation examples cited above and recited at theappropriate point, and taking account of the general details relating tothe preparation of[(5-phenyl-1-(Heteroaryl)-1H-1,2,4-triazol-3-yl)oxy]acetic acidderivatives, the compounds listed below are obtained:

Table I.1: Preferred compounds of the formula (I.1) are the compoundsI.1-1 to I.1-24 in which Q has the meanings from table 1 indicated inthe respective row. Thus, the compounds I.1-1 to I.1-24 of table I.1 aredefined by the meaning of the respective entry nos. 1 to 24 for Q fromtable 1.

TABLE 1 No. Q 1 Q-2.1 2 Q-2.2 3 Q-2.3 4 Q-2.4 5 Q-2.5 6 Q-2.6 7 Q-2.7 8Q-2.10 9 Q-2.11 10 Q-2.12 11 Q-2.13 12 Q-2.14 13 Q-2.15 14 Q-2.17 15Q-2.18 16 Q-2.19 17 Q-2.21 18 Q-2.22 19 Q-2.24 20 Q-2.25 21 Q-2.56 22Q-2.57 23 Q-2.59 24 Q-2.60

Table I.2: Preferred compounds of the formula (I.2) are the compoundsI.2-1 to I.2-24 in which Q has the meanings from table 1 indicated inthe respective row. Thus, the compounds I.2-1 to I.2-24 of table I.2 aredefined by the meaning of the respective entry nos. 1 to 24 for Q fromtable 1.

Table I.3: Preferred compounds of the formula (I.3) are the compoundsI.3-1 to I.3-24 in which Q has the meanings from table 1 indicated inthe respective row. Thus, the compounds I.3-1 to I.3-24 of table I.3 aredefined by the meaning of the respective entry nos. 1 to 24 for Q fromtable 1.

Table I.4: Preferred compounds of the formula (I.4) are the compoundsI.4-1 to I.4-24 in which Q has the meanings from table 1 indicated inthe respective row. Thus, the compounds I.4-1 to I.4-24 of table I.4 aredefined by the meaning of the respective entry nos. 1 to 24 for Q fromtable 1.

Table I.5: Preferred compounds of the formula (I.5) are the compoundsI.5-1 to I.5-24 in which Q has the meanings from table 1 indicated inthe respective row. Thus, the compounds I.5-1 to I.5-24 of table I.5 aredefined by the meaning of the respective entry nos. 1 to 24 for Q fromtable 1.

Table I.6: Preferred compounds of the formula (I.6) are the compoundsI.6-1 to I.6-24 in which Q has the meanings from table 1 indicated inthe respective row. Thus, the compounds I.6-1 to I.6-24 of table I.6 aredefined by the meaning of the respective entry nos. 1 to 24 for Q fromtable 1.

Table I.7: Preferred compounds of the formula (I.7) are the compoundsI.7-1 to I.7-24 in which Q has the meanings from table 1 indicated inthe respective row. Thus, the compounds I.7-1 to I.7-24 of table I.7 aredefined by the meaning of the respective entry nos. 1 to 24 for Q fromtable 1.

Table I.8: Preferred compounds of the formula (I.8) are the compoundsI.8-1 to I.8-24 in which Q has the meanings from table 1 indicated inthe respective row. Thus, the compounds I.8-1 to I.8-24 of table I.8 aredefined by the meaning of the respective entry nos. 1 to 24 for Q fromtable 1.

Table I.9: Preferred compounds of the formula (I.9) are the compoundsI.9-1 to I.9-24 in which Q has the meanings from table 1 indicated inthe respective row. Thus, the compounds I.9-1 to I.9-24 of table I.9 aredefined by the meaning of the respective entry nos. 1 to 24 for Q fromtable 1.

Table I.10: Preferred compounds of the formula (I.10) are the compoundsI.10-1 to I.10-24 in which Q has the meanings from table 1 indicated inthe respective row. Thus, the compounds I.10-1 to I.10-24 of table I.10are defined by the meaning of the respective entry nos. 1 to 24 for Qfrom table 1.

Table I.11: Preferred compounds of the formula (I.11) are the compoundsI.11-1 to I.11-24 in which Q has the meanings from table 1 indicated inthe respective row. Thus, the compounds I.11-1 to I.11-24 of table I.11are defined by the meaning of the respective entry nos. 1 to 24 for Qfrom table 1.

Table I.12: Preferred compounds of the formula (I.12) are the compoundsI.12-1 to I.12-24 in which Q has the meanings from table 1 indicated inthe respective row. Thus, the compounds I.12-1 to I.12-24 of

Table I.13: Preferred compounds of the formula (I.13) are the compoundsI.13-1 to I.13-24 in which Q has the meanings from table 1 indicated inthe respective row. Thus, the compounds I.13-1 to I.13-24 of table I.13are defined by the meaning of the respective entry nos. 1 to 24 for Qfrom table 1.

Table I.14: Preferred compounds of the formula (I.14) are the compoundsI.14-1 to I.14-24 in which Q has the meanings from table 1 indicated inthe respective row. Thus, the compounds I.14-1 to I.14-24 of table I.14are defined by the meaning of the respective entry nos. 1 to 24 for Qfrom table 1.

Table I.15: Preferred compounds of the formula (I.15) are the compoundsI.15-1 to I.15-24 in which Q has the meanings from table 1 indicated inthe respective row. Thus, the compounds I.15-1 to I.15-24 of

Table I.16: Preferred compounds of the formula (I.16) are the compoundsI.16-1 to I.16-24 in which Q has the meanings from table 1 indicated inthe respective row. Thus, the compounds I.16-1 to I.16-24 of table I.16are defined by the meaning of the respective entry nos. 1 to 24 for Qfrom table 1.

Table I.17: Preferred compounds of the formula (I.17) are the compoundsI.17-1 to I.17-24 in which Q has the meanings from table 1 indicated inthe respective row. Thus, the compounds I.17-1 to I.17-24 of table I.17are defined by the meaning of the respective entry nos. 1 to 24 for Qfrom table 1.

Table I.18: Preferred compounds of the formula (I.18) are the compoundsI.18-1 to I.18-24 in which Q has the meanings from table 1 indicated inthe respective row. Thus, the compounds I.18-1 to I.18-24 of

Table I.19: Preferred compounds of the formula (I.19) are the compoundsI.19-1 to I.19-24 in which Q has the meanings from table 1 indicated inthe respective row. Thus, the compounds I.19-1 to I.19-24 of table I.19are defined by the meaning of the respective entry nos. 1 to 24 for Qfrom table 1.

Table I.20: Preferred compounds of the formula (I.20) are the compoundsI.20-1 to I.20-24 in which Q has the meanings from table 1 indicated inthe respective row. Thus, the compounds I.20-1 to I.20-24 of table I.20are defined by the meaning of the respective entry nos. 1 to 24 for Qfrom table 1.

Table I.21: Preferred compounds of the formula (I.21) are the compoundsI.21-1 to I.21-24 in which Q has the meanings from table 1 indicated inthe respective row. Thus, the compounds I.21-1 to I.21-24 of

Table I.22: Preferred compounds of the formula (I.22) are the compoundsI.22-1 to I.22-24 in which Q has the meanings from table 1 indicated inthe respective row. Thus, the compounds I.22-1 to I.22-24 of table I.22are defined by the meaning of the respective entry nos. 1 to 24 for Qfrom table 1.

Table I.23: Preferred compounds of the formula (I.23) are the compoundsI.23-1 to I.23-24 in which Q has the meanings from table 1 indicated inthe respective row. Thus, the compounds I.23-1 to I.23-24 of table I.23are defined by the meaning of the respective entry nos. 1 to 22 for Qfrom table 1.

Table I.24: Preferred compounds of the formula (I.24) are the compoundsI.24-1 to I.24-24 in which Q has the meanings from table 1 indicated inthe respective row. Thus, the compounds I.24-1 to I.24-24 of

Table I.25: Preferred compounds of the formula (I.25) are the compoundsI.25-1 to I.25-24 in which Q has the meanings from table 1 indicated inthe respective row. Thus, the compounds I.25-1 to I.25-24 of table I.25are defined by the meaning of the respective entry nos. 1 to 24 for Qfrom table 1.

Table I.26: Preferred compounds of the formula (I.26) are the compoundsI.26-1 to I.26-24 in which Q has the meanings from table 1 indicated inthe respective row. Thus, the compounds I.26-1 to I.26-24 of table I.26are defined by the meaning of the respective entry nos. 1 to 24 for Qfrom table 1.

Table I.27: Preferred compounds of the formula (I.27) are the compoundsI.27-1 to I.27-24 in which Q has the meanings from table 1 indicated inthe respective row. Thus, the compounds I.27-1 to I.27-24 of

Table I.28: Preferred compounds of the formula (I.28) are the compoundsI.28-1 to I.28-24 in which Q has the meanings from table 1 indicated inthe respective row. Thus, the compounds I.28-1 to I.28-24 of table I.28are defined by the meaning of the respective entry nos. 1 to 24 for Qfrom table 1.

Table I.29: Preferred compounds of the formula (I.29) are the compoundsI.29-1 to I.29-24 in which Q has the meanings from table 1 indicated inthe respective row. Thus, the compounds I.29-1 to I.29-24 of table I.29are defined by the meaning of the respective entry nos. 1 to 24 for Qfrom table 1.

Table I.30: Preferred compounds of the formula (I.30) are the compoundsI.30-1 to I.30-24 in which Q has the meanings from table 1 indicated inthe respective row. Thus, the compounds I.30-1 to I.30-24 of

Table I.31: Preferred compounds of the formula (I.31) are the compoundsI.31-1 to I.31-24 in which Q has the meanings from table 1 indicated inthe respective row. Thus, the compounds I.31-1 to I.31-24 of table I.31are defined by the meaning of the respective entry nos. 1 to 24 for Qfrom table 1.

Table I.32: Preferred compounds of the formula (I.32) are the compoundsI.32-1 to I.32-24 in which Q has the meanings from table 1 indicated inthe respective row. Thus, the compounds I.32-1 to I.32-24 of table I.32are defined by the meaning of the respective entry nos. 1 to 24 for Qfrom table 1.

Table I.33: Preferred compounds of the formula (I.33) are the compoundsI.33-1 to I.33-24 in which Q has the meanings from table 1 indicated inthe respective row. Thus, the compounds I.33-1 to I.33-24 of

Table I.34: Preferred compounds of the formula (I.34) are the compoundsI.34-1 to I.34-24 in which Q has the meanings from table 1 indicated inthe respective row. Thus, the compounds I.34-1 to I.34-24 of table I.34are defined by the meaning of the respective entry nos. 1 to 24 for Qfrom table 1.

Table I.35: Preferred compounds of the formula (I.35) are the compoundsI.35-1 to I.35-24 in which Q has the meanings from table 1 indicated inthe respective row. Thus, the compounds I.35-1 to I.35-24 of table I.35are defined by the meaning of the respective entry nos. 1 to 24 for Qfrom table 1.

Table I.36: Preferred compounds of the formula (I.36) are the compoundsI.36-1 to I.36-24 in which Q has the meanings from table 1 indicated inthe respective row. Thus, the compounds I.36-1 to I.36-24 of

Table I.37: Preferred compounds of the formula (I.37) are the compoundsI.37-1 to I.37-24 in which Q has the meanings from table 1 indicated inthe respective row. Thus, the compounds I.37-1 to I.37-24 of table I.37are defined by the meaning of the respective entry nos. 1 to 24 for Qfrom table 1.

Table I.38: Preferred compounds of the formula (I.38) are the compoundsI.38-1 to I.38-24 in which Q has the meanings from table 1 indicated inthe respective row. Thus, the compounds I.38-1 to I.38-24 of table I.38are defined by the meaning of the respective entry nos. 1 to 24 for Qfrom table 1.

Table I.39: Preferred compounds of the formula (I.39) are the compoundsI.39-1 to I.39-24 in which Q has the meanings from table 1 indicated inthe respective row. Thus, the compounds I.39-1 to I.39-24 of

Table I.40: Preferred compounds of the formula (I.40) are the compoundsI.40-1 to I.40-24 in which Q has the meanings from table 1 indicated inthe respective row. Thus, the compounds I.40-1 to I.40-24 of table I.40are defined by the meaning of the respective entry nos. 1 to 24 for Qfrom table 1.

Table I.41: Preferred compounds of the formula (I.41) are the compoundsI.41-1 to I.41-24 in which Q has the meanings from table 1 indicated inthe respective row. Thus, the compounds I.41-1 to I.41-24 of table I.41are defined by the meaning of the respective entry nos. 1 to 24 for Qfrom table 1.

Table I.42: Preferred compounds of the formula (I.42) are the compoundsI.42-1 to I.42-24 in which Q has the meanings from table 1 indicated inthe respective row. Thus, the compounds I.42-1 to I.42-24 of

Table I.43: Preferred compounds of the formula (I.4) are the compoundsI.43-1 to I.43-24 in which Q has the meanings from table 1 indicated inthe respective row. Thus, the compounds I.43-1 to I.43-24 of table 1.43are defined by the meaning of the respective entry nos. 1 to 24 for Qfrom table 1.

Table I.44: Preferred compounds of the formula (I.44) are the compoundsI.44-1 to I.44-24 in which Q has the meanings from table 1 indicated inthe respective row. Thus, the compounds I.44-1 to I.44-24 of table I.44are defined by the meaning of the respective entry nos. 1 to 24 for Qfrom table 1.

Table I.45: Preferred compounds of the formula (I.45) are the compoundsI.45-1 to I.45-24 in which Q has the meanings from table 1 indicated inthe respective row. Thus, the compounds I.45-1 to I.45-24 of

Table I.46: Preferred compounds of the formula (I.46) are the compoundsI.46-1 to I.46-24 in which Q has the meanings from table 1 indicated inthe respective row. Thus, the compounds I.46-1 to I.46-24 of table I.46are defined by the meaning of the respective entry nos. 1 to 24 for Qfrom table 1.

Table I.47: Preferred compounds of the formula (I.47) are the compoundsI.47-1 to I.47-24 in which Q has the meanings from table 1 indicated inthe respective row. Thus, the compounds I.47-1 to I.47-24 of table I.47are defined by the meaning of the respective entry nos. 1 to 24 for Qfrom table 1.

Table I.48: Preferred compounds of the formula (I.48) are the compoundsI.48-1 to I.48-24 in which Q has the meanings from table 1 indicated inthe respective row. Thus, the compounds I.48-1 to I.48-24 of

Table I.49: Preferred compounds of the formula (I.49) are the compoundsI.49-1 to I.49-24 in which Q has the meanings from table 1 indicated inthe respective row. Thus, the compounds I.49-1 to I.49-24 of table I.49are defined by the meaning of the respective entry nos. 1 to 24 for Qfrom table 1.

Table I.50: Preferred compounds of the formula (I.50) are the compoundsI.50-1 to I.50-24 in which Q has the meanings from table 1 indicated inthe respective row. Thus, the compounds I.50-1 to I.50-24 of table I.50are defined by the meaning of the respective entry nos. 1 to 24 for Qfrom table 1.

Table I.51: Preferred compounds of the formula (I.51) are the compoundsI.51-1 to I.51-24 in which Q has the meanings from table 1 indicated inthe respective row. Thus, the compounds I.51-1 to I.51-24 of

Table I.52: Preferred compounds of the formula (I.52) are the compoundsI.52-1 to I.52-24 in which Q has the meanings from table 1 indicated inthe respective row. Thus, the compounds I.52-1 to I.52-24 of table I.52are defined by the meaning of the respective entry nos. 1 to 24 for Qfrom table 1.

Table I.53: Preferred compounds of the formula (I.53) are the compoundsI.53-1 to I.53-24 in which Q has the meanings from table 1 indicated inthe respective row. Thus, the compounds I.53-1 to I.53-24 of table I.53are defined by the meaning of the respective entry nos. 1 to 24 for Qfrom table 1.

Table I.54: Preferred compounds of the formula (I.54) are the compoundsI.54-1 to I.54-24 in which Q has the meanings from table 1 indicated inthe respective row. Thus, the compounds I.54-1 to I.54-24 of

Table I.55: Preferred compounds of the formula (I.55) are the compoundsI.55-1 to I.55-24 in which Q has the meanings from table 1 indicated inthe respective row. Thus, the compounds I.55-1 to I.55-24 of table I.55are defined by the meaning of the respective entry nos. 1 to 24 for Qfrom table 1.

Table I.56: Preferred compounds of the formula (I.56) are the compoundsI.56-1 to I.56-24 in which Q has the meanings from table 1 indicated inthe respective row. Thus, the compounds I.56-1 to I.56-24 of table I.56are defined by the meaning of the respective entry nos. 1 to 24 for Qfrom table 1.

Table I.57: Preferred compounds of the formula (I.57) are the compoundsI.57-1 to I.57-24 in which Q has the meanings from table 1 indicated inthe respective row. Thus, the compounds I.57-1 to I.57-24 of

Table I.58: Preferred compounds of the formula (I.58) are the compoundsI.58-1 to I.58-24 in which Q has the meanings from table 1 indicated inthe respective row. Thus, the compounds I.58-1 to I.58-24 of table I.58are defined by the meaning of the respective entry nos. 1 to 24 for Qfrom table 1.

Table I.59: Preferred compounds of the formula (I.59) are the compoundsI.59-1 to I.59-24 in which Q has the meanings from table 1 indicated inthe respective row. Thus, the compounds I.59-1 to I.59-24 of table I.59are defined by the meaning of the respective entry nos. 1 to 24 for Qfrom table 1.

Table I.60: Preferred compounds of the formula (I.60) are the compoundsI.60-1 to I.60-24 in which Q has the meanings from table 1 indicated inthe respective row. Thus, the compounds I.60-1 to I.60-24 of

Table I.61: Preferred compounds of the formula (I.61) are the compoundsI.61-1 to I.61-24 in which Q has the meanings from table 1 indicated inthe respective row. Thus, the compounds I.61-1 to I.61-24 of table I.61are defined by the meaning of the respective entry nos. 1 to 24 for Qfrom table 1.

Table I.62: Preferred compounds of the formula (I.62) are the compoundsI.62-1 to I.62-24 in which Q has the meanings from table 1 indicated inthe respective row. Thus, the compounds I.62-1 to I.62-24 of table I.62are defined by the meaning of the respective entry nos. 1 to 24 for Qfrom table 1.

Table I.63: Preferred compounds of the formula (I.63) are the compoundsI.63-1 to I.63-24 in which Q has the meanings from table 1 indicated inthe respective row. Thus, the compounds I.63-1 to I.63-24 of table I.63are defined by the meaning of the respective entry nos. 1 to 24 for Qfrom table 1.

Table I.64: Preferred compounds of the formula (I.64) are the compoundsI.64-1 to I.64-24 in which Q has the meanings from table 1 indicated inthe respective row. Thus, the compounds I.64-1 to I.64-24 of table I.64are defined by the meaning of the respective entry nos. 1 to 24 for Qfrom table 1.

Table I.65: Preferred compounds of the formula (I.65) are the compoundsI.65-1 to I.65-24 in which Q has the meanings from table 1 indicated inthe respective row. Thus, the compounds I.65-1 to I.65-24 of table I.65are defined by the meaning of the respective entry nos. 1 to 24 for Qfrom table 1.

Table I.66: Preferred compounds of the formula (I.66) are the compoundsI.66-1 to I.66-24 in which Q has the meanings from table 1 indicated inthe respective row. Thus, the compounds I.66-1 to I.66-24 of

Table I.67: Preferred compounds of the formula (I.67) are the compoundsI.67-1 to I.67-24 in which Q has the meanings from table 1 indicated inthe respective row. Thus, the compounds I.67-1 to I.67-24 of table I.67are defined by the meaning of the respective entry nos. 1 to 24 for Qfrom table 1.

Table I.68: Preferred compounds of the formula (I.68) are the compoundsI.68-1 to I.68-24 in which Q has the meanings from table 1 indicated inthe respective row. Thus, the compounds I.68-1 to I.68-24 of table I.68are defined by the meaning of the respective entry nos. 1 to 24 for Qfrom table 1.

Table I.69: Preferred compounds of the formula (I.69) are the compoundsI.69-1 to I.69-24 in which Q has the meanings from table 1 indicated inthe respective row. Thus, the compounds I.69-1 to I.69-24 of

Table I.70: Preferred compounds of the formula (I.70) are the compoundsI.70-1 to I.70-24 in which Q has the meanings from table 1 indicated inthe respective row. Thus, the compounds I.70-1 to I.70-24 of table I.70are defined by the meaning of the respective entry nos. 1 to 24 for Qfrom table 1.

Table I.71: Preferred compounds of the formula (I.71) are the compoundsI.71-1 to I.71-24 in which Q has the meanings from table 1 indicated inthe respective row. Thus, the compounds I.71-1 to I.71-24 of table I.71are defined by the meaning of the respective entry nos. 1 to 24 for Qfrom table 1.

Table I.72: Preferred compounds of the formula (I.72) are the compoundsI.72-1 to I.72-24 in which Q has the meanings from table 1 indicated inthe respective row. Thus, the compounds I.72-1 to I.72-24 of table I.72are defined by the meaning of the respective entry nos. 1 to 24 for Qfrom table 1.

Table I.73: Preferred compounds of the formula (I.73) are the compoundsI.73-1 to I.73-24 in which Q has the meanings from table 1 indicated inthe respective row. Thus, the compounds I.73-1 to I.73-24 of table I.73are defined by the meaning of the respective entry nos. 1 to 24 for Qfrom table 1.

Table I.74: Preferred compounds of the formula (I.74) are the compoundsI.74-1 to I.74-24 in which Q has the meanings from table 1 indicated inthe respective row. Thus, the compounds I.74-1 to I.74-24 of table I.74are defined by the meaning of the respective entry nos. 1 to 24 for Qfrom table 1.

Table I.75: Preferred compounds of the formula (I.75) are the compoundsI.75-1 to I.75-24 in which Q has the meanings from table 1 indicated inthe respective row. Thus, the compounds I.75-1 to I.75-24 of table I.75are defined by the meaning of the respective entry nos. 1 to 24 for Qfrom table 1.

Table I.76: Preferred compounds of the formula (I.76) are the compoundsI.76-1 to I.76-24 in which Q has the meanings from table 1 indicated inthe respective row. Thus, the compounds I.76-1 to I.76-24 of table I.76are defined by the meaning of the respective entry nos. 1 to 24 for Qfrom table 1.

Table I.77: Preferred compounds of the formula (I.77) are the compoundsI.77-1 to I.77-24 in which Q has the meanings from table 1 indicated inthe respective row. Thus, the compounds I.77-1 to I.77-24 of table I.77are defined by the meaning of the respective entry nos. 1 to 24 for Qfrom table 1.

Spectroscopic data of selected table examples:

Selected detailed synthesis examples for the inventive compounds of thegeneral formula (I) are adduced below. The ¹H NMR, ¹³C-NMR and ¹⁹F-NMRspectroscopy data reported for the chemical examples described in thesections which follow (400 MHz for ¹H NMR and 150 MHz for ¹³C-NMR and375 MHz for ¹⁹F-NMR, solvent CDCl₃, CD₃OD or d₆-DMSO, internal standard:tetramethylsilane δ=0.00 ppm) were obtained on a Bruker instrument, andthe signals listed have the meanings given below: br=broad; s=singlet,d=doublet, t=triplet, dd=doublet of doublets, ddd=doublet of a doubletof doublets, m=multiplet, q=quartet, quint=quintet, sext=sextet,sept=septet, dq=doublet of quartets, dt=doublet of triplets. In the caseof diastereomer mixtures, either the significant signals for each of thetwo diastereomers are reported or the characteristic signal of the maindiastereomer is reported. The abbreviations used for chemical groupshave, for example, the following meanings: Me=CH₃, Et=CH₂CH₃,t-Hex=C(CH₃)₂CH(CH₃)₂, t-Bu=C(CH₃)₃, n-Bu=unbranched butyl,n-Pr=unbranched propyl, i-Pr=branched propyl, c-Pr=cyclopropyl,c-Hex=cyclohexyl.

The spectroscopic data listed hereinafter for selected table exampleswere evaluated via conventional ¹H NMR interpretation or via NMR peaklist methods.

Conventional ¹H NMR Interpretation Example No. I.48-23

¹H-NMR (400 MHz, DMSO-d₆ δ, ppm) 13.13 (bs, 1H), 8.57 (m, 1H), 8.19 (dd,1H), 7.64-7.54 (m, 3H), 7.43 (dd, 1H), 4.87 (s, 2H).

Example No. I.40-10

¹H-NMR (400 MHz, CDCl₃ δ, ppm) 8.12 (d, 1H), 7.80 (dd, 1H), 7.72 (dd,1H), 7.68 (m, 1H), 7.01 (m, 1H), 6.79 (m, 1H), 4.97 (s, 2H), 3.82 (s,3H).

Example No. I.41-9

¹H-NMR (400 MHz, CDCl₃ δ, ppm) 8.09 (d, 1H), 7.80 (dd, 1H), 7.66 (m,1H), 7.07-6.98 (m, 2H), 6.83-6.78 (m, 2H), 4.93 (s, 2H), 4.28 (q, 2H),1.30 (t, 3H).

Example No. I.48-11

¹H-NMR (400 MHz, CDCl₃ δ, ppm) 8.29 (d, 1H), 7.69-7.60 (m, 2H), 7.39(dd, 1H), 7.31 (m, 1H), 7.10 (m, 1H), 4.98 (s, 2H).

Example No. I.40-11

¹H-NMR (400 MHz, CDCl₃ δ, ppm) 8.03 (d, 1H), 7.77-7.68 (m, 2H), 7.55 (m,1H), 7.01 (m, 1H), 6.77 (m, 1H), 4.97 (s, 2H), 3.82 (s, 3H).

Example No. I.46-23

¹H-NMR (400 MHz, CDCl₃ δ, ppm) 8.48 (d, 1H), 7.83 (dd, 1H), 7.58 (m,1H), 7.38 (m, 1H), 7.23 (m, 1H), 7.02 (dd, 1H), 4.95 (s, 2H), 3.81 (s,3H).

Example No. I.42-9

¹H-NMR (400 MHz, DMSO-d₆ δ, ppm) 13.12 (bs, 1H), 8.27 (d, 1H), 8.04 (m,1H), 7.72 (m, 1H), 7.43-7.27 (m, 3H), 4.88 (s, 2H).

Example No. I.48-10

¹H-NMR (400 MHz, DMSO-d₆ δ, ppm) 13.17 (bs, 1H), 8.36 (d, 1H), 8.18 (dd,1H), 7.78 (d, 1H), 7.69 (m, 1H), 7.56 (m, 1H), 7.46 (m, 1H), 4.91 (s,2H).

Example No. I.49-9

¹H-NMR (400 MHz, CDCl₃ δ, ppm) 8.09 (d, 1H), 7.82 (m, 1H), 7.62 (m, 1H),7.29 (m, 1H), 7.08 (m, 1H), 7.00 (m, 1H), 4.95 (s, 2H), 3.82 (s, 3H).

Example No. I.42-23

¹H-NMR (400 MHz, DMSO-d₆ δ, ppm) 13.11 (bs, 1H), 8.56 (dd, 1H), 8.19(dd, 1H), 7.66-7.60 (m, 2H), 7.38 (m, 1H), 7.23 (m, 1H), 4.86 (s, 2H).

Example No. I.46-10

¹H-NMR (400 MHz, CDCl₃ δ, ppm) 8.12 (d, 1H), 7.80 (dd, 1H), 7.72 (dd,1H), 7.63 (dd, 1H), 7.28 (dd, 1H), 7.07 (dd, 1H), 4.97 (s, 2H), 3.82 (s,3H).

Example No. I.47-9

¹H-NMR (400 MHz, CDCl₃ δ, ppm) 8.09 (d, 1H), 7.81 (m, 1H), 7.61 (m, 1H),7.30 (m, 1H), 7.10 (dd, 1H), 7.00 (m, 1H), 4.93 (s, 2H), 4.28 (q, 2H),1.30 (t, 3H).

Example No. I.48-9

¹H-NMR (400 MHz, DMSO-d₆ δ, ppm) 13.12 (bs, 1H), 8.28 (d, 1H), 8.06 (m,1H), 7.66 (m, 1H), 7.59 (m, 1H), 7.49 (m, 1H), 7.34 (m, 1H), 4.86 (s,2H).

Example No. I.40-21

¹H-NMR (400 MHz, CDCl₃ δ, ppm) 8.48 (m, 1H), 7.83 (m, 1H), 7.62 (m, 1H),7.38 (m, 1H), 6.97 (m, 1H), 6.73 (m, 1H), 4.95 (s, 2H), 3.81 (s, 3H).

Example No. I.46-8

¹H-NMR (400 MHz, CDCl₃ δ, ppm) 8.26 (d, 1H), 7.68-7.60 (m, 2H), 7.38 (d,1H), 7.31 (dd, 1H), 7.10 (dd, 1H), 4.95 (s, 2H), 3.82 (s, 3H).

NMR Peak List Method

The 1H NMR data of selected examples are noted in the form of 1H NMRpeak lists. For each signal peak, first the δ value in ppm and then thesignal intensity in round brackets are listed. The δ value/signalintensity number pairs for different signal peaks are listed withseparation from one another by semicolons.

The peak list for one example therefore takes the form of:

-   -   δ₁ (intensity₁); δ₂ (intensity₂); . . . ; δ_(i) (intensity_(i));        . . . ; δ_(n) (intensity_(n))

The intensity of sharp signals correlates with the height of the signalsin a printed example of an NMR spectrum in cm and shows the true ratiosof the signal intensities. In the case of broad signals, several peaksor the middle of the signal and the relative intensity thereof may beshown in comparison to the most intense signal in the spectrum.

For calibration of the chemical shift of ¹H NMR spectra, we usetetramethylsilane and/or the chemical shift of the solvent, particularlyin the case of spectra which are measured in DMSO. Therefore, thetetramethylsilane peak may but need not occur in NMR peak lists.

The lists of the ¹H NMR peaks are similar to the conventional ¹H NMRprintouts and thus usually contain all peaks listed in a conventionalNMR interpretation.

In addition, like conventional ¹H NMR printouts, they may show solventsignals, signals of stereoisomers of the target compounds which arelikewise provided by the invention, and/or peaks of impurities.

In the reporting of compound signals within the delta range of solventsand/or water, our lists of ¹H NMR peaks show the standard solvent peaks,for example peaks of DMSO in DMSO-D₆ and the peak of water, whichusually have a high intensity on average.

The peaks of stereoisomers of the target compounds and/or peaks ofimpurities usually have a lower intensity on average than the peaks ofthe target compounds (for example with a purity of >90%).

Such stereoisomers and/or impurities may be typical of the particularpreparation process. Their peaks can thus help in identifyingreproduction of our preparation process with reference to “by-productfingerprints”.

An expert calculating the peaks of the target compounds by known methods(MestreC, ACD simulation, but also with empirically evaluated expectedvalues) can, if required, isolate the peaks of the target compounds,optionally using additional intensity filters. This isolation would besimilar to the relevant peak picking in conventional 1H NMRinterpretation.

Further details of ¹H NMR peak lists can be found in the Researchdisclosure Database Number 564025.

I.57-22: ¹H-NMR(300.1 MHz, d₆-DMSO): δ = 12.3937 (0.5); 9.2480 (5.6);9.2263 (5.8); 8.4325 (0.7); 8.2959 (5.3); 8.2734 (5.8); 8.2539 (0.6);7.7257 (0.5); 7.7012 (0.8); 7.6745 (1.9); 7.6510 (3.3); 7.6256 (2.6);7.6039 (1.1); 7.4338 (0.7); 7.4088 (2.8); 7.3830 (3.7); 7.3710 (3.5);7.3463 (4.7); 7.3331 (6.9); 7.3008 (13.9); 7.2743 (12.3); 7.2615 (6.5);7.2363 (5.4); 7.1221 (1.4); 7.0973 (3.3); 7.0747 (4.5); 7.0606 (4.3);6.9997 (3.1); 6.9759 (5.5); 6.9531 (11.4); 6.9243 (15.5); 6.8958 (7.8);6.8719 (3.2); 6.8488 (3.8); 6.8250 (2.4); 6.7449 (0.5); 6.6061 (0.4);4.5766 (0.5); 4.3590 (0.4); 4.3133 (0.5); 4.3021 (0.5); 4.2682 (0.5);4.2449 (0.5); 4.1884 (0.9); 4.1153 (10.9); 4.0355 (1.2); 3.9754 (16.0);3.8965 (1.3); 3.8294 (0.8); 3.7693 (0.8); 3.7405 (1.0); 3.6499 (1.2);3.3287 (243.7); 3.2142 (2.7); 3.1688 (2.0); 3.1235 (1.6); 3.0996 (1.4);3.0795 (1.3); 3.0277 (1.3); 2.9926 (1.2); 2.9734 (1.2); 2.9586 (1.2);2.9448 (1.2); 2.8896 (1.4); 2.8544 (1.5); 2.7986 (1.8); 2.7262 (4.2);2.5006 (396.1); 2.3887 (1.9); 2.3477 (1.6); 2.2709 (3.0); 2.2167 (0.9);2.1786 (0.9); 2.1672 (0.8); 2.1355 (0.8); 2.0914 (0.6); 2.0438 (0.6);2.0169 (0.5); 2.0011 (0.5); 1.9738 (0.6); 1.9628 (0.6); 1.9550 (0.5);1.8867 (2.4); 1.8221 (0.6); 1.7825 (0.6); 1.7660 (0.6); 1.7548 (0.5);1.7160 (0.4); 1.7029 (0.4); 1.6921 (0.4); 1.6808 (0.4); 1.6412 (0.4);1.6176 (0.4); 1.5901 (0.5); 1.5781 (0.4); 1.5286 (0.4); 1.4249 (0.5);1.3681 (0.4); 1.2931 (0.4); 1.2532 (0.5); 1.2432 (0.7); 1.2358 (1.0);1.2249 (0.7); 1.2129 (0.5); 1.1445 (2.1); 1.0718 (0.6); 1.0553 (0.6);1.0466 (0.6); 1.0248 (0.5); 1.0054 (0.6); 0.9782 (0.6); 0.8976 (0.4);0.8874 (0.4); 0.7967 (0.4); 0.5598 (0.4); −0.0016 (2.3); −3.5425 (0.4);−3.5753 (0.4) I.40-2: ¹H-NMR(400.6 MHz, CDCl₃): δ = 8.6034 (0.8); 8.5998(0.8); 8.5914 (0.8); 8.5878 (0.8); 8.5092 (1.1); 8.5033 (1.1); 7.7098(0.7); 7.7060 (0.8); 7.7034 (0.8); 7.6995 (0.8); 7.6893 (0.9); 7.6855(0.9); 7.6828 (1.4); 7.6789 (1.1); 7.6668 (0.7); 7.6612 (0.8); 7.6476(0.9); 7.6448 (0.9); 7.6410 (0.6); 7.6254 (0.6); 7.3752 (0.8); 7.3734(0.8); 7.3632 (0.8); 7.3614 (0.8); 7.3547 (0.8); 7.3529 (0.8); 7.3426(0.7); 7.3409 (0.7); 7.2636 (27.7); 7.0318 (0.7); 7.0291 (0.5); 7.0283(0.5); 7.0257 (0.8); 6.8196 (0.6); 6.8135 (0.5); 6.7981 (0.6); 6.7944(0.6); 6.7922 (0.6); 6.7885 (0.6); 6.7731 (0.6); 6.7670 (0.5); 4.9602(8.3); 3.8212 (16.0); 3.8141 (0.6); 1.6095 (2.2); 1.2845 (0.6); 1.2549(1.2); −0.0002 (9.0) I.40-22: ¹H-NMR(300.1 MHz, d₆-DMSO): δ = 8.3804(2.2); 8.3572 (2.2); 7.4826 (0.7); 7.4540 (1.5); 7.4327 (1.7); 7.4097(1.7); 7.3854 (1.6); 7.3743 (1.4); 7.3484 (1.5); 7.2151 (0.9); 7.2071(0.9); 7.1763 (1.5); 7.1500 (1.9); 7.1360 (1.7); 7.1259 (2.0); 7.1116(2.0); 7.1023 (1.2); 7.0875 (1.0); 7.0362 (0.8); 7.0134 (1.5); 6.9853(0.8); 4.7327 (8.8); 3.7436 (16.0); 3.5869 (0.7); 3.3314 (9.3); 3.3078(2.5); 2.5079 (27.4); 2.5020 (35.7); 2.4963 (25.7); 2.0763 (0.5); 1.2331(0.5); −0.0008 (7.2) I.4-22: ¹H-NMR(300.1 MHz, d₆-DMSO): δ = 8.3870(2.0); 8.3640 (2.2); 8.1362 (0.5); 7.4120 (0.4); 7.3875 (1.7); 7.3632(3.0); 7.3485 (2.9); 7.3423 (3.3); 7.3250 (2.4); 7.3179 (2.1); 7.1396(1.0); 7.1248 (1.3); 7.1156 (1.7); 7.0974 (3.2); 7.0687 (3.8); 7.0428(1.3); 7.0366 (1.1); 4.7834 (0.4); 4.7432 (6.0); 4.6890 (0.5); 3.7489(16.0); 3.6957 (0.5); 3.6890 (0.6); 3.5712 (0.7); 3.3364 (24.5); 2.5147(2.4); 2.5090 (4.7); 2.5031 (6.3); 2.4973 (4.5); 2.0764 (11.3); −0.0004(0.6) I.1-22: ¹H-NMR(300.1 MHz, d₆-DMSO): δ = 8.2143 (2.1); 8.2128(2.1); 8.1906 (2.3); 8.1713 (2.3); 8.1669 (2.9); 8.1619 (1.3); 8.1511(0.9); 8.1444 (3.2); 8.1390 (2.3); 7.5503 (0.5); 7.5455 (0.4); 7.5366(0.4); 7.5262 (1.7); 7.5177 (1.6); 7.5077 (1.1); 7.5026 (1.8); 7.4947(1.5); 7.4797 (2.8); 7.4773 (2.8); 7.4575 (2.6); 7.4529 (3.4); 7.4352(0.5); 7.4297 (1.1); 7.4244 (0.6); 7.3891 (0.4); 6.9748 (0.8); 6.9597(0.8); 6.9502 (1.2); 6.9353 (1.2); 6.9257 (0.7); 6.9105 (0.6); 5.3890(7.1); 4.9956 (0.6); 3.7465 (0.3); 3.7381 (0.4); 3.7123 (1.5); 3.6764(16.0); 3.6508 (0.4); 3.6465 (0.3); 3.6304 (0.4); 3.6212 (0.3); 3.6048(0.8); 3.5927 (0.6); 3.5795 (0.3); 3.5685 (0.4); 3.4657 (0.3); 3.4558(0.3); 3.3719 (457.6); 3.3123 (0.4); 2.5167 (10.1); 2.5108 (19.6);2.5049 (26.1); 2.4989 (17.9); 2.4931 (8.1); 2.0750 (3.2); 1.2337 (0.4);−0.0002 (1.0) I.55-22: ¹H-NMR(300.1 MHz, d₆-DMSO): δ = 8.4406 (1.9);8.4178 (2.0); 7.4413 (0.5); 7.4211 (1.8); 7.4138 (1.2); 7.3969 (2.5);7.3909 (2.3); 7.3866 (2.2); 7.3686 (1.6); 7.3615 (2.2); 7.3413 (0.6);7.1839 (1.0); 7.1691 (1.2); 7.1601 (1.5); 7.1455 (1.4); 7.1359 (0.9);7.1212 (0.7); 7.0351 (1.5); 7.0062 (2.5); 6.9776 (1.3); 4.7845 (8.4);4.7386 (0.8); 3.7663 (16.0); 3.5637 (1.6); 3.3356 (8.8); 2.5033 (5.0);2.0768 (3.1) I.46-22: ¹H-NMR(400.2 MHz, d₆-DMSO): δ = 8.3930 (2.1);8.3758 (2.2); 7.4213 (1.4); 7.4129 (1.4); 7.4012 (2.6); 7.3924 (2.8);7.3865 (3.0); 7.3665 (2.9); 7.2298 (1.8); 7.2254 (1.8); 7.2090 (1.5);7.2046 (1.4); 7.1551 (0.8); 7.1441 (1.0); 7.1371 (1.4); 7.1263 (1.5);7.1191 (0.9); 7.1081 (0.8); 4.7367 (8.3); 3.7466 (16.0); 3.5891 (0.8);3.3351 (41.4); 3.3114 (3.9); 2.5117 (7.8); 2.5074 (15.7); 2.5030 (21.0);2.4985 (15.0); 2.4942 (7.1); 2.0772 (0.5); 1.7541 (0.6); 0.0001 (2.0)I.6-22: ¹H-NMR(300.1 MHz, d₆-DMSO): δ = 13.2965 (0.3); 13.2071 (0.4);13.1912 (0.4); 13.1600 (0.4); 13.1177 (0.3); 8.4117 (6.7); 8.3888 (6.9);8.1553 (0.4); 8.1316 (0.4); 8.0424 (0.7); 8.0223 (0.9); 7.9896 (0.4);7.8715 (0.4); 7.8651 (0.5); 7.7451 (0.4); 7.7227 (0.7); 7.6997 (0.6);7.6776 (0.7); 7.6545 (0.8); 7.6292 (0.6); 7.5240 (0.3); 7.4980 (0.4);7.4734 (0.6); 7.4300 (1.3); 7.4094 (1.4); 7.3741 (6.0); 7.3496 (12.5);7.3364 (8.4); 7.3293 (11.4); 7.3117 (7.3); 7.3044 (8.1); 7.2766 (1.0);7.2640 (0.5); 7.2554 (0.4); 7.2384 (0.5); 7.2167 (0.4); 7.1287 (3.5);7.1138 (4.4); 7.1047 (6.0); 7.0879 (10.9); 7.0581 (12.8); 7.0319 (4.5);7.0270 (4.2); 6.9585 (0.3); 5.2560 (1.0); 4.6150 (16.0); 4.5420 (2.2);3.3229 (7.7); 3.1461 (0.4); 2.7339 (0.5); 2.7280 (0.7); 2.7220 (0.5);2.5138 (45.6); 2.5079 (87.7); 2.5020 (115.5); 2.4960 (79.8); 2.4903(37.1); 2.2780 (0.5); 2.2716 (0.7); 2.2660 (0.5); 2.0743 (5.8); 1.2351(0.6); 1.1470 (0.4); 0.0109 (0.4); −0.0002 (9.2) I.40-11: ¹H-NMR(400.6MHz, d₆-DMSO): δ = 8.3202 (3.0); 8.3127 (3.1); 8.0327 (1.1); 8.0252(1.0); 8.0123 (1.3); 8.0103 (1.5); 8.0048 (1.2); 8.0028 (1.4); 7.9900(1.4); 7.9825 (1.2); 7.8209 (1.7); 7.8111 (1.8); 7.7986 (1.4); 7.7976(1.4); 7.7887 (1.4); 7.7878 (1.3); 7.7499 (0.7); 7.7338 (0.8); 7.7287(1.3); 7.7126 (1.4); 7.7076 (0.9); 7.6915 (0.8); 7.3892 (0.7); 7.3830(0.8); 7.3659 (0.9); 7.3624 (1.0); 7.3599 (1.0); 7.3564 (0.9); 7.3393(0.8); 7.3331 (0.8); 7.2783 (0.6); 7.2763 (0.6); 7.2704 (0.6); 7.2567(1.1); 7.2554 (1.2); 7.2500 (1.1); 7.2358 (0.6); 7.2338 (0.6); 7.2292(0.5); 5.7575 (16.0); 4.9056 (10.5); 2.5135 (5.3); 2.5089 (11.6); 2.5043(16.2); 2.4998 (11.2); 2.4952 (5.0); −0.0002 (10.3) I.47-5: ¹H-NMR(400.6MHz, CDCl₃): δ = 9.1884 (6.7); 8.7235 (16.0); 7.6796 (1.5); 7.6606(1.7); 7.6589 (1.9); 7.6400 (1.7); 7.3488 (1.3); 7.3471 (1.2); 7.3438(1.3); 7.3423 (1.3); 7.3279 (1.1); 7.3263 (1.1); 7.3230 (1.2); 7.3215(1.1); 7.2630 (10.4); 7.1320 (1.6); 7.1271 (1.5); 7.1075 (1.6); 7.1027(1.5); 5.3008 (0.8); 4.9398 (12.2); 4.3160 (1.6); 4.2982 (5.0); 4.2804(5.0); 4.2626 (1.6); 1.5749 (2.4); 1.3281 (6.3); 1.3104 (13.2); 1.2925(6.2); 0.0697 (1.8); −0.0002 (15.4) I.46-11: ¹H-NMR(400.6 MHz, CDCl₃): δ= 8.0396 (1.7); 8.0387 (1.6); 8.0323 (1.8); 8.0313 (1.7); 7.7751 (0.8);7.7741 (0.8); 7.7654 (0.9); 7.7642 (0.8); 7.7528 (1.0); 7.7517 (0.9);7.7431 (1.1); 7.7420 (0.9); 7.6672 (1.1); 7.6482 (1.3); 7.6467 (1.4);7.6277 (1.2); 7.5878 (0.8); 7.5804 (0.8); 7.5691 (0.9); 7.5654 (0.7);7.5618 (0.8); 7.5581 (0.7); 7.5468 (0.7); 7.5395 (0.6); 7.2864 (1.0);7.2848 (0.9); 7.2814 (1.0); 7.2800 (0.9); 7.2654 (1.0); 7.2630 (3.8);7.2607 (1.0); 7.2592 (0.9); 7.0668 (1.2); 7.0619 (1.2); 7.0422 (1.2);7.0373 (1.2); 5.2997 (2.4); 4.9649 (8.5); 3.8160 (16.0); 0.0710 (3.8);−0.0002 (5.1) I.47-20: ¹H-NMR(400.6 MHz, CDCl₃): δ = 8.1450 (1.6);8.1309 (1.6); 8.1242 (1.6); 8.1101 (1.6); 7.6508 (1.8); 7.6319 (2.1);7.6303 (2.4); 7.6114 (2.1); 7.5353 (1.6); 7.5296 (1.7); 7.5116 (1.7);7.5058 (1.6); 7.2862 (1.5); 7.2846 (1.5); 7.2813 (1.6); 7.2798 (1.6);7.2654 (1.6); 7.2623 (20.4); 7.0814 (2.0); 7.0765 (1.9); 7.0570 (2.0);7.0522 (1.9); 6.9806 (1.2); 6.9748 (1.2); 6.9665 (1.2); 6.9609 (2.3);6.9553 (1.2); 6.9470 (1.3); 6.9412 (1.1); 5.2999 (5.4); 4.9454 (15.3);4.3166 (1.9); 4.2988 (6.1); 4.2810 (6.2); 4.2631 (2.0); 1.3240 (7.9);1.3199 (0.6); 1.3062 (16.0); 1.3021 (1.1); 1.2884 (7.6); 1.2842 (0.7);0.0704 (1.5); −0.0002 (12.4) I.47-11: ¹H-NMR(400.6 MHz, CDCl₃): δ =8.0374 (2.8); 8.0363 (2.7); 8.0300 (3.0); 8.0290 (2.7); 7.7756 (1.4);7.7744 (1.2); 7.7658 (1.4); 7.7647 (1.3); 7.7533 (1.7); 7.7520 (1.6);7.7435 (1.7); 7.7424 (1.5); 7.6641 (1.8); 7.6450 (2.2); 7.6435 (2.3);7.6245 (2.0); 7.5853 (1.4); 7.5780 (1.3); 7.5666 (1.5); 7.5630 (1.2);7.5593 (1.4); 7.5556 (1.1); 7.5444 (1.2); 7.5370 (1.1); 7.2851 (1.6);7.2834 (1.5); 7.2801 (1.6); 7.2786 (1.5); 7.2627 (7.8); 7.2594 (1.6);7.2579 (1.4); 7.0665 (1.9); 7.0616 (1.8); 7.0419 (1.9); 7.0371 (1.8);5.2998 (5.8); 4.9406 (14.7); 4.3092 (1.9); 4.2913 (5.9); 4.2735 (6.0);4.2557 (2.0); 1.5851 (1.0); 1.3163 (7.7); 1.2984 (16.0); 1.2806 (7.5);0.0706 (3.5); −0.0002 (9.7) I.46-5: ¹H-NMR(400.6 MHz, CDCl₃): δ = 9.1908(4.7); 8.7253 (11.4); 7.6824 (1.1); 7.6633 (1.3); 7.6617 (1.4); 7.6427(1.3); 7.3500 (1.0); 7.3484 (0.9); 7.3451 (1.0); 7.3436 (0.9); 7.3292(0.8); 7.3275 (0.8); 7.3242 (0.9); 7.3227 (0.8); 7.2627 (9.0); 7.1324(1.2); 7.1276 (1.1); 7.1079 (1.2); 7.1031 (1.1); 5.3007 (2.3); 4.9638(8.3); 3.8259 (16.0); 1.5736 (1.0); 1.2596 (0.8); 0.8819 (1.0); 0.0697(1.2); −0.0002 (13.0); −0.0028 (0.5) I.48-5: ¹H-NMR(400.6 MHz, d₆-DMSO):δ = 9.2544 (7.2); 8.9046 (16.0); 7.7240 (1.0); 7.7034 (1.7); 7.6835(1.3); 7.6384 (1.1); 7.6335 (1.2); 7.6128 (1.1); 7.6079 (1.2); 7.5129(1.1); 7.5116 (1.1); 7.5073 (1.1); 7.4919 (0.9); 7.4906 (0.9); 7.4864(0.9); 4.9102 (6.6); 3.3234 (1.3); 2.5201 (0.5); 2.5113 (7.8); 2.5068(17.2); 2.5022 (24.2); 2.4976 (16.6); 2.4930 (7.3); 2.1834 (0.6); 1.3558(5.8); −0.0002 (18.4); −0.0085 (0.5) I.48-11: ¹H-NMR(400.6 MHz,d₆-DMSO): δ = 8.3326 (3.0); 8.3251 (3.1); 8.0378 (1.1); 8.0303 (1.0);8.0175 (1.3); 8.0154 (1.5); 8.0100 (1.1); 8.0079 (1.4); 7.9952 (1.4);7.9876 (1.2); 7.8281 (1.6); 7.8272 (1.6); 7.8183 (1.8); 7.8058 (1.4);7.8047 (1.4); 7.7959 (1.4); 7.7949 (1.3); 7.7071 (1.6); 7.6867 (2.7);7.6669 (1.9); 7.5692 (1.7); 7.5642 (1.8); 7.5437 (1.7); 7.5387 (1.9);7.4705 (1.7); 7.4694 (1.8); 7.4648 (1.7); 7.4498 (1.4); 7.4486 (1.5);7.4441 (1.4); 5.7572 (16.0); 4.9061 (10.1); 3.3248 (0.8); 2.5252 (0.6);2.5206 (0.8); 2.5118 (10.1); 2.5073 (22.2); 2.5027 (31.1); 2.4981(21.4); 2.4935 (9.4); 0.0080 (0.6); −0.0002 (23.2); −0.0085 (0.7)

The invention also provides the method of protecting crop plants oruseful plants from phytotoxic effects of agrochemicals, such aspesticides, or herbicides in particular, which cause damage to the cropplants or useful plants, characterized in that compounds of the generalformula (I) or salts thereof are employed as safeners, preference beinggiven to applying an effective amount of the compounds of the generalformula (I) or salts thereof to the plants, parts of plants or seeds (orseed material) thereof.

The compounds of the general formula (I) safeners) as specified aboveare suitable for use together with active ingredients (pesticides) forselective control of harmful organisms in a number of crop cultures, forexample in economically important crops such as cereal (wheat, barley,triticale, rye, rice, maize, millet/sorghum), sugar beet, sugar cane,oilseed rape, cotton, sunflower, peas, beans and soya.

The herbicide-safener combinations with safeners of the general formula(I) are also suitable for control of harmful plants on beds and areas ofuseful plants and ornamental plants, for example lawn areas with utilitylawns or decorative lawns, specifically ryegrass, bluegrass or bermudagrass.

Also of interest in respect of the useful plants and crop plants inwhich the herbicide-safener combinations comprising the aforementionedcompounds of the general formula (I) can be used are mutant crops thatare wholly or partially tolerant or transgenic crops that are wholly orpartially tolerant to some pesticides, for example maize crops resistantto glufosinate or glyphosate, or soya crops that are resistant toimidazolinones that have a plant-damaging effect.

However, the particular benefit of the safeners of the general formula(I) used in a novel manner is their effective action in crops that arenot normally sufficiently tolerant to the pesticides to be employed.

For common use with pesticides, the compounds of the general formula (I)can be deployed simultaneously or in any sequence with the activeingredients, and are then capable of reducing or entirely preventingdamaging side effects of these active ingredients in the case of cropplants without impairing or significantly reducing the efficacy of theseactive ingredients with respect to unwanted harmful organisms.

It is also possible here to significantly reduce or entirely preventdamage resulting from the use of more than one pesticide, for example bymore than one herbicide or by herbicides in combination withinsecticides or fungicides.

This can quite considerably extend the field of use of conventionalpesticides.

If the compositions of the invention contain pesticides, thesecompositions, at appropriate dilution, are applied either directly tothe growing area, to the already germinated harmful plants and/or usefulplants, or to the already emerged harmful plants and/or useful plants.

If the compositions of the invention do not contain any pesticide, thesecompositions may be used by what is called the tankmix method, meaningthat the user mixes and dilutes the separately formulated products(=useful plant-protecting composition and pesticide) immediately priorto application to the area to be treated, or before the application of apesticide, or after the application of a pesticide, or for seedpretreatment, i.e., for example, for dressing of the useful plant seed.

Preference is given to prompt application of the safener with thepesticide, especially when the safener is applied to the plants afterthe herbicide.

The advantageous effects of the compounds of the general formula (I) areobserved when they are used together with the pesticides by thepre-emergence or post-emergence method, for example in the case ofsimultaneous application as a tankmix or as a co-formulation or in aseparate application in parallel or successively (split application). Itis also possible to repeat the application more than once. It cansometimes also be sensible to combine a pre-emergence application with apost-emergence application. One option is usually employment aspost-emergence application to the useful plant or crop plant withsimultaneous or later application of the pesticide. Another option is toemploy the inventive compounds (I) in seed dressing, (dip) treatment ofseedlings (e.g. rice) or treatment of other propagation material (e.g.potato tubers).

When the compounds of the general formula (I) are employed incombination with herbicides, it is often the case that not only thesafener effect but also boosts in herbicidal action against harmfulplants are observed. Moreover, the growth of the useful plants and cropplants is improved in many cases, and it is possible to increase theharvest yields.

The compositions of the invention may contain one or more pesticides.Examples of useful pesticides include herbicides, insecticides,fungicides, acaricides and nematicides which, when employed alone, wouldeach result in phytotoxic damage to the crop plants or where damagewould be likely.

Of particular interest are the corresponding active pesticidalingredients from the group of the herbicides, insecticides, acaricides,nematicides and fungicides, especially herbicides.

The weight ratio of safeners (of the general formula (I)) to pesticidemay be varied within wide limits and is generally in the range from1:100 to 100:1, preferably 1:20 to 20:1, especially 1:10 to 10:1. Theoptimal weight ratio of safener to pesticide depends both on therespective safener used and the respective pesticide and on the type ofuseful plant or crop plant to be protected. According to the pesticideused and type of useful plant to be protected, the required applicationrate of safener may be varied within wide limits and is generally in therange from 0.001 to 10 kg, preferably 0.01 to 1 kg, especially 0.01 to0.2 kg, of safener per hectare. The amounts and weight ratios needed fora successful treatment can be ascertained by simple preliminary tests.

In the case of seed dressing, for example, 0.005 to 20 g of safener (ofthe general formula (I)) per kilogram of seed, preferably 0.01 to 10 gof safener per kilogram of seed, especially 0.05 to 5 g of safener perkilogram of seed, are used.

When solutions of safeners (of the general formula (I)) are utilized inseed treatment and the seed or seedlings are wetted with the solutions,the suitable concentration is generally in the range from 1 to 10 000ppm, preferably 100 to 1000 ppm, based on weight.

The amounts and weight ratios needed for a successful treatment can beascertained by simple preliminary tests.

The safeners of the general formula (I) can be formulated in a customarymanner, separately or together with the pesticides.

Also provided, therefore, are the useful plant- or crop plant-protectingcompositions.

Preference is given to the joint use of safener and pesticide,especially that of safener and herbicide as a finished formulation oremployment by the tankmix method.

Likewise preferred is the employment of the safener of the generalformula (I) in seed treatment with later application of pesticides,preferably herbicides, after sowing by the pre- or post-emergencemethod.

The compounds of the general formula (I) or salts thereof can be used assuch or in the form of their preparations (formulations) in acombination with other pesticidally active substances, for exampleinsecticides, acaricides, nematicides, herbicides, fungicides, safeners,fertilizers and/or growth regulators, for example in the form of afinished formulation or of tank mixes.

The combination formulations can be produced on the basis of theabovementioned formulations, taking account of the physical propertiesand stabilities of the active ingredients to be combined.

Combination partners usable for the compounds of the invention in mixedformulations or in a tankmix are, for example, known active ingredientsbased on inhibition of, for example, acetolactate synthase, acetyl-CoAcarboxylase, cellulose synthase, enolpyruvylshikimate-3-phosphatesynthase, glutamine synthetase, p-hydroxyphenylpyruvate dioxygenase,phytoene desaturase, photosystem I, photosystem II or protoporphyrinogenoxidase, as known, for example, from Weed Research 26 (1986) 441-445 or“The Pesticide Manual”, 16th edition, The British Crop ProtectionCouncil and the Royal Soc. of Chemistry, 2006, and literature citedtherein.

Known herbicides or plant growth regulators which can be combined withthe compounds of the invention are, for example, the following, wheresaid active ingredients are referred to either by their “common name” inaccordance with the International Organization for Standardization (ISO)or by the chemical name or by the code number. They always encompass allthe use forms, for example acids, salts, esters and also all isomericforms such as stereoisomers and optical isomers, even if they are notmentioned explicitly.

Examples of such herbicidal mixing partners are:

acetochlor, acifluorfen, acifluorfen-sodium, aclonifen, alachlor,allidochlor, alloxydim, alloxydim-sodium, ametryn, amicarbazone,amidochlor, amidosulfuron,4-amino-3-chloro-6-(4-chloro-2-fluoro-3-methylphenyl)-5-fluoropyridine-2-carboxylicacid, aminocyclopyrachlor, aminocyclopyrachlor-potassium,aminocyclopyrachlor-methyl, aminopyralid, amitrole, ammoniumsulfamate,anilofos, asulam, atrazine, azafenidin, azimsulfuron, beflubutamid,benazolin, benazolin-ethyl, benfluralin, benfuresate, bensulfuron,bensulfuron-methyl, bensulide, bentazone, benzobicyclon, benzofenap,bicyclopyron, bifenox, bilanafos, bilanafos-sodium, bispyribac,bispyribac-sodium, bromacil, bromobutide, bromofenoxim, bromoxynil,bromoxynil-butyrate, -potassium, -heptanoate and -octanoate, busoxinone,butachlor, butafenacil, butamifos, butenachlor, butralin, butroxydim,butylate, cafenstrole, carbetamide, carfentrazone, carfentrazone-ethyl,chloramben, chlorbromuron, chlorfenac, chlorfenac-sodium, chlorfenprop,chlorflurenol, chlorflurenol-methyl, chloridazon, chlorimuron,chlorimuron-ethyl, chlorophthalim, chlorotoluron, chlorthal-dimethyl,chlorsulfuron, cinidon, cinidon-ethyl, cinmethylin, cinosulfuron,clacyfos, clethodim, clodinafop, clodinafop-propargyl, clomazone,clomeprop, clopyralid, cloransulam, cloransulam-methyl, cumyluron,cyanamide, cyanazine, cycloate, cyclopyrimorate, cyclosulfamuron,cycloxydim, cyhalofop, cyhalofop-butyl, cyprazine, 2,4-D, 2,4-D-butotyl,-butyl, -dimethylammonium, -diolamine, -ethyl, 2-ethylhexyl, -isobutyl,-isooctyl, -isopropylammonium, -potassium, -triisopropanolammonium and-trolamine, 2,4-DB, 2,4-DB-butyl, -dimethylammonium, isooctyl,-potassium and -sodium, daimuron (dymron), dalapon, dazomet, n-decanol,desmedipham, detosyl-pyrazolate (DTP), dicamba, dichlobenil,2-(2,4-dichlorobenzyl)-4,4-dimethyl-1,2-oxazolidin-3-one,2-(2,5-dichlorobenzyl)-4,4-dimethyl-1,2-oxazolidin-3-one, dichlorprop,dichlorprop-P, diclofop, diclofop-methyl, diclofop-P-methyl, diclosulam,difenzoquat, diflufenican, diflufenzopyr, diflufenzopyr-sodium,dimefuron, dimepiperate, dimethachlor, dimethametryn, dimethenamid,dimethenamid-P, dimetrasulfuron, dinitramine, dinoterb, diphenamid,diquat, diquat-dibromid, dithiopyr, diuron, DNOC, endothal, EPTC,esprocarb, ethalfluralin, ethametsulfuron, ethametsulfuron-methyl,ethiozin, ethofumesate, ethoxyfen, ethoxyfen-ethyl, ethoxysulfuron,etobenzanid, F-9600, F-5231, i.e.N-[2-chloro-4-fluoro-5-[4-(3-fluoropropyl)-4,5-dihydro-5-oxo-1H-tetrazol-1-yl]-phenyl]ethanesulfonamide,F-7967, i.e.3-[7-chloro-5-fluoro-2-(trifluoromethyl)-1H-benzimidazol-4-yl]-1-methyl-6-(trifluoromethyl)pyrimidine-2,4(1H,3H)-dione,fenoxaprop, fenoxaprop-P, fenoxaprop-ethyl, fenoxaprop-P-ethyl,fenoxasulfone, fenquinotrione, fentrazamide, flamprop,flamprop-M-isopropyl, flamprop-M-methyl, flazasulfuron, florasulam,fluazifop, fluazifop-P, fluazifop-butyl, fluazifop-P-butyl,flucarbazone, flucarbazone-sodium, flucetosulfuron, fluchloralin,flufenacet, flufenpyr, flufenpyr-ethyl, flumetsulam, flumiclorac,flumiclorac-pentyl, flumioxazin, fluometuron, flurenol, flurenol-butyl,-dimethylammonium and -methyl, fluoroglycofen, fluoroglycofen-ethyl,flupropanate, flupyrsulfuron, flupyrsulfuron-methyl-sodium, fluridone,flurochloridone, fluroxypyr, fluroxypyr-meptyl, flurtamone, fluthiacet,fluthiacet-methyl, fomesafen, fomesafen-sodium, foramsulfuron, fosamine,glufosinate, glufosinate-ammonium, glufosinate-P-sodium,glufosinate-P-ammonium, glufosinate-P-sodium, glyphosate,glyphosate-ammonium, -isopropylammonium, -diammonium, -dimethylammonium,-potassium, -sodium and -trimesium, H-9201, i.e.O-(2,4-dimethyl-6-nitrophenyl) O-ethyl isopropylphosphoramidothioate,halauxifen, halauxifen-methyl, halosafen, halosulfuron,halosulfuron-methyl, haloxyfop, haloxyfop-P, haloxyfop-ethoxyethyl,haloxyfop-P-ethoxyethyl, haloxyfop-methyl, haloxyfop-P-methyl,hexazinone, HW-02, i.e. 1-(dimethoxyphosphoryl)ethyl(2,4-dichlorophenoxy)acetate, imazamethabenz, Imazamethabenz-methyl,imazamox, imazamox-ammonium, imazapic, imazapic-ammonium, imazapyr,imazapyr-isopropylammonium, imazaquin, imazaquin-ammonium, imazethapyr,imazethapyr-immonium, imazosulfuron, indanofan, indaziflam,iodosulfuron, iodosulfuron-methyl-sodium, ioxynil, ioxynil-octanoate,-potassium and sodium, ipfencarbazone, isoproturon, isouron, isoxaben,isoxaflutole, karbutilate, KUH-043, i.e.3-({[5-(difluoromethyl)-1-methyl-3-(trifluoromethyl)-1H-pyrazol-4-yl]methyl}sulfonyl)-5,5-dimethyl-4,5-dihydro-1,2-oxazole,ketospiradox, lactofen, lenacil, linuron, MCPA, MCPA-butotyl,-dimethylammonium, -2-ethylhexyl, -isopropylammonium, -potassium and-sodium, MCPB, MCPB-methyl, -ethyl and -sodium, mecoprop,mecoprop-sodium, and -butotyl, mecoprop-P, mecoprop-P-butotyl,-dimethylammonium, -2-ethylhexyl and -potassium, mefenacet, mefluidide,mesosulfuron, mesosulfuron-methyl, mesotrione, methabenzthiazuron,metam, metamifop, metamitron, metazachlor, metazosulfuron,methabenzthiazuron, methiopyrsulfuron, methiozolin, methylisothiocyanate, metobromuron, metolachlor, S-metolachlor, metosulam,metoxuron, metribuzin, metsulfuron, metsulfuron-methyl, molinat,monolinuron, monosulfuron, monosulfuron-ester, MT-5950, i.e.N-[3-chloro-4-(1-methylethyl)phenyl]-2-methylpentanamide, NGGC-011,napropamide, NC-310, i.e.4-(2,4-dichlorobenzoyl)-1-methyl-5-benzyloxypyrazole, neburon,nicosulfuron, nonanoic acid (pelargonic acid), norflurazon, oleic acid(fatty acids), orbencarb, orthosulfamuron, oryzalin, oxadiargyl,oxadiazon, oxasulfuron, oxaziclomefon, oxyfluorfen, paraquat, paraquatdichloride, pebulate, pendimethalin, penoxsulam, pentachlorphenol,pentoxazone, pethoxamid, petroleum oils, phenmedipham, picloram,picolinafen, pinoxaden, piperophos, pretilachlor, primisulfuron,primisulfuron-methyl, prodiamine, profoxydim, prometon, prometryn,propachlor, propanil, propaquizafop, propazine, propham, propisochlor,propoxycarbazone, propoxycarbazone-sodium, propyrisulfuron, propyzamide,prosulfocarb, prosulfuron, pyraclonil, pyraflufen, pyraflufen-ethyl,pyrasulfotole, pyrazolynate (pyrazolate), pyrazosulfuron,pyrazosulfuron-ethyl, pyrazoxyfen, pyribambenz, pyribambenz-isopropyl,pyribambenz-propyl, pyribenzoxim, pyributicarb, pyridafol, pyridate,pyriftalid, pyriminobac, pyriminobac-methyl, pyrimisulfan, pyrithiobac,pyrithiobac-sodium, pyroxasulfone, pyroxsulam, quinclorac, quinmerac,quinoclamine, quizalofop, quizalofop-ethyl, quizalofop-P,quizalofop-P-ethyl, quizalofop-P-tefuryl, rimsulfuron, saflufenacil,sethoxydim, siduron, simazine, simetryn, SL-261, sulcotrion,sulfentrazone, sulfometuron, sulfometuron-methyl, sulfosulfuron,SYP-249, i.e. 1-ethoxy-3-methyl-1-oxobut-3-en-2-yl5-[2-chloro-4-(trifluoromethyl)phenoxy]-2-nitrobenzoate, SYP-300, i.e.1-[7-fluoro-3-oxo-4-(prop-2-yn-1-yl)-3,4-dihydro-2H-1,4-benzoxazin-6-yl]-3-propyl-2-thioxoimidazolidine-4,5-dione,2,3,6-TBA, TCA (trifluoroacetic acid), TCA-sodium, tebuthiuron,tefuryltrione, tembotrione, tepraloxydim, terbacil, terbucarb,terbumeton, terbuthylazin, terbutryn, thenylchlor, thiazopyr,thiencarbazone, thiencarbazone-methyl, thifensulfuron,thifensulfuron-methyl, thiobencarb, tiafenacil, tolpyralate,topramezone, tralkoxydim, triafamone, tri-allate, triasulfuron,triaziflam, tribenuron, tribenuron-methyl, triclopyr, trietazine,trifloxysulfuron, trifloxysulfuron-sodium, trifludimoxazin, trifluralin,triflusulfuron, triflusulfuron-methyl, tritosulfuron, urea sulfate,vernolate, XDE-848, ZJ-0862, i.e.3,4-dichloro-N-{2-[(4,6-dimethoxypyrimidin-2-yl)oxy]benzyl}aniline, andthe following compounds:

Examples of plant growth regulators as possible mixing partners are:

acibenzolar, acibenzolar-S-methyl, 5-aminolevulinic acid, ancymidol,6-benzylaminopurine, brassinolide, catechol, chlormequat chloride,cloprop, cyclanilide, 3-(cycloprop-1-enyl)propionic acid, daminozide,dazomet, n-decanol, dikegulac, dikegulac-sodium, endothal,endothal-dipotassium, -disodium, and mono(N,N-dimethylalkylammonium),ethephon, flumetralin, flurenol, flurenol-butyl, flurprimidol,forchlorfenuron, gibberellic acid, inabenfide, indole-3-acetic acid(IAA), 4-indol-3-ylbutyric acid, isoprothiolane, probenazole, jasmonicacid, jasmonic acid methyl ester, maleic hydrazide, mepiquat chloride,1-methylcyclopropene, 2-(1-naphthyl)acetamide, 1-naphthylacetic acid,2-naphthyloxyacetic acid, nitrophenolate mixture,4-oxo-4[(2-phenylethyl)amino]butyric acid, paclobutrazole,N-phenylphthalamic acid, prohexadione, prohexadione-calcium,prohydrojasmone, salicylic acid, strigolactone, tecnazene, thidiazuron,triacontanol, trinexapac, trinexapac-ethyl, tsitodef, uniconazole,uniconazole-P.

In the case of employment as active ingredient formulations orco-formulations, these generally contain, as the case may be, therespectively customary stickers, wetters, dispersants, emulsifiers,penetrants, preservatives, antifreezes and solvents, fillers, carriersand dyes, defoamers, evaporation inhibitors, and pH and viscositymodifiers.

The compounds of the general formula (I) and combinations thereof withone or more of the pesticides mentioned may be formulated in variousways depending on the defined physicochemical and biological parameters.

Suitable examples of types of formulation include:

emulsifiable concentrates that are produced by dissolving the activeingredients in an organic solvent, for example butanol, cyclohexanone,dimethylformamide, xylene, or else relatively high-boiling hydrocarbonsor mixtures of the organic solvents, with addition of one or more ionicand/or nonionic surfactants (emulsifiers).

Suitable emulsifiers are, for example, calcium alkylarylsulfonates,fatty acid polyglycol esters, alkylaryl polyglycol ethers, fatty alcoholpolyglycol ethers, propylene oxide-ethylene oxide condensation products,alkyl polyethers, sorbitan esters and polyoxyethylene sorbitan fattyacid esters;

-   -   dusting products that are obtained by grinding the active        ingredients with finely divided solid inorganic or organic        substances, e.g. talc, natural clays, such as kaolin, bentonite        and pyrophyllite, diatomaceous earth or flours;    -   water- or oil-based suspension concentrates that can be        produced, for example, by wet grinding by means of bead mills;    -   water-soluble powders;    -   water-soluble concentrates;    -   granules, such as water-soluble granules, water-dispersible        granules and granules for broadcasting and soil application;    -   wettable powders which, as well as the active ingredient, also        contain diluents or inert substances and surfactants;    -   capsule suspensions and microcapsules;    -   ultralow-volume formulations.

The abovementioned formulation types are known to the person skilled inthe art and are described, for example, in: K. Martens, “Spray DryingHandbook”, 3rd ed., G. Goodwin Ltd., London. 1979; W. van Valkenburg,“Pesticide Formulations”, Marcel Dekker, N.Y. 1973; Winacker-Ktichler,“Chemische Technologie” [Chemical Technology], volume 7, C. HanserVerlag Munich, 4th edition 1986; “Perry's Chemical Engineer's Handbook”,5th ed., McGraw-Hill, N.Y. 1973, pages 8-57.

The necessary formulation auxiliaries such as inert materials,surfactants, solvents and further additives are likewise known and aredescribed, for example, in:

McCutcheon's “Detergents and Emulsifiers Annual”, MC Publ. Corp.,Ridgewood N.J.; C. Marsden, “Solvents Guide”, 2nd ed., Interscience,N.Y. 1963; H. von Olphen, “Introduction to Clay Colloid Chemistry”, 2nded., J. Wiley & Sons, N.Y.; Schonfeldt, “GrenzflachenaktiveAthylenoxidaddukte” [Interface-active Ethylene Oxide Adducts], Wiss.Verlagsgesellschaft, Stuttgart 1976; Sisley and Wood, “Encyclopedia ofSurface Active Agents”, Chem. Publ. Co. Inc., N.Y. 1964; Watkins,“Handbook of Insecticide Dust Diluents and Carriers”, 2nd ed., DarlandBooks, Caldwell N.J.; Winnacker-Ktichler, “Chemische Technologie”,volume 7, C. Hanser Verlag Munich, 4th edition 1986.

Apart from the aforementioned formulation auxiliaries, the usefulplant-protecting compositions may, as the case may be, contain customarywetters, stickers, dispersants, penetrants, emulsifiers, preservatives,antifreezes, fillers, carriers and dyes, defoamers, evaporationinhibitors, and pH or viscosity modifiers.

According to the type of formulation, the useful plant-protectingcompositions contain generally 0.1% to 99% by weight, especially 0.2% to95% by weight, of one or more safeners of the general formula (I) or acombination of safener and pesticide.

They additionally contain 1% to 99.9%, especially 4% to 99.5%, by weightof one or more solid or liquid additives and 0% to 25%, especially 0.1to 25%, by weight of a surfactant. In emulsifiable concentrates, theactive ingredient concentration, i.e. the concentration of safenerand/or pesticide, is generally 1% to 90%, especially 5% to 80%, byweight.

Dusting products typically contain 1% to 30%, preferably 5% to 20%, byweight of active ingredient. In wettable powders, the active ingredientconcentration is generally 10% to 90% by weight.

In the water-dispersible granules, the content of active ingredient is,for example, between 1% and 95% by weight, preferably between 10% and80% by weight.

For application, the formulations in the commercial form are diluted ifappropriate in a customary manner, for example with water in the case ofwettable powders, emulsifiable concentrates, dispersions andwater-dispersible granules.

Preparations in dust form, granules and sprayable solutions are notnormally diluted further with other inert substances prior toapplication.

The required application rate of the safeners of the general formula (I)varies with external conditions including temperature, humidity and thetype of herbicide used.

In the examples which follow, which illustrate but do not limit theinvention, statements of amount are based on weight unless definedotherwise.

Examples 1. Formulation Examples

1.1 Dusting Product

A dusting product is obtained by mixing 10 parts by weight of a compoundof the general formula (I) (safener) or of an active ingredient mixturecomposed of a pesticide (e.g. a herbicide) and a safener of the generalformula (I) and 90 parts by weight of talc as inert substance, andcomminuting in a bead mill

1.2 Water-Dispersible Powder

A readily water-dispersible wettable powder is obtained by mixing 25parts by weight of a compound of the general formula (I) or of an activeingredient mixture of a pesticide (e.g. a herbicide) and a safener ofthe general formula (I), 64 parts by weight of kaolin-containing quartzas an inert substance, 10 parts by weight of potassium lignosulfonateand 1 part by weight of sodium oleoylmethyltaurate as a wetting agentand dispersant, and grinding the mixture in a pinned-disk mill

1.3 Water-Dispersible Granules

A water-dispersible dispersion concentrate is obtained by mixing 20parts by weight of a compound of the general formula (I) or of an activeingredient mixture of a pesticide (e.g. a herbicide) and a safener ofthe formula (I) with 6 parts by weight of alkylphenol polyglycol ether(®Triton X 207), 3 parts by weight of isotridecanol polyglycol ether and71 parts by weight of paraffinic mineral oil, and grinding in a frictionball mill to a fineness below 5 microns.

1.4 Emulsifiable Concentrate

An emulsifiable concentrate is obtained from 15 parts by weight of acompound of the general formula (I) or of an active ingredient mixturecomposed of a pesticide (e.g. a herbicide) and a safener of the generalformula (I), 75 parts by weight of cyclohexanone as solvent and 10 partsby weight of ethoxylated nonylphenol as emulsifier.

1.5 Water-Dispersible Granules

Water-dispersible granules are obtained by mixing

-   -   75 parts by weight of a safener of the general formula (I) or a        mixture of a pesticide and a safener of the general formula (I),    -   10 ″ of calcium lignosulfonate,    -   5 ″ of sodium laurylsulfate,    -   3 ″ of polyvinyl alcohol and    -   7 ″ of polyvinyl alcohol and    -   7 ″ of kaolin,        grinding the mixture in a pinned-disk mill, and granulating the        powder in a fluidized bed by spray application of water as a        granulating liquid.

Water-dispersible granules are also obtained by homogenizing andcomminuting, in a colloid mill,

-   -   25 parts by weight of a safener of the general formula (I) or a        mixture of a pesticide and a safener of the general formula (I),    -   5 ″ of sodium 2,2′-dinaphthylmethane-6,6′-disulfonate,    -   2 ″ of sodium oleoylmethyltaurinate,    -   17 ″ of calcium carbonate,    -   50 ″ of water and    -   1 part by weight of polyvinyl alcohol,        then grinding the mixture in a bead mill and atomizing and        drying the suspension thus obtained in a spray tower by means of        a one-phase nozzle.

2. Biological Examples

2.1 Relative Action of Selected Compounds of the Invention Using theExample of Reduction of Damage by Mesosulfuron-Methyl on Summer Barley(HORVS)

The seeds of the crop plants to be treated are laid out in sandy loam inplastic pots (diameter ˜4 cm), covered with soil and grown in agreenhouse under good conditions for germination and growth. The trialplants were treated at the early leaf stage (BBCH10-BBCH12). In thecourse of this, the inventive compounds of the general formula (I)formulated in the form of wettable powders (WP) were sprayed onto theabove-ground parts of the plants as an aqueous suspension with a waterapplication rate corresponding to 800 l/ha with addition of wettingagent (e.g. 0.2% Genapol-LRO or 0.2% Mero) in the specified dose.

This was followed by the application of the herbicide. For this purpose,mesosulfuron-methyl, formulated in the form of water-dispersiblegranules (WG), was sprayed onto the above-ground parts of the plants inthe form of an aqueous dispersion with a water application ratecorresponding to 800 l/ha with addition of wetting agent (e.g. 0.2%Genapol-LRO or 1 l/ha Biopower) in a dose of 40-60 g/ha. The dose of theherbicide was chosen here such that it causes visually apparent damage(min. 30%, max. 75%) compared to untreated crop plants at the evaluationtime on a control group of crop plants without safener treatment thatwere included in the same trial.

After application, the plants were cultivated under good growthconditions in a greenhouse. 9-13 days after application, the efficacy ofthe test compounds was assessed visually. For this purpose, theappearance of the plants treated with the test compound and herbicidewas compared to the corresponding herbicide controls (without safener;with clearly visible damage) and the untreated controls (withoutdamage). The damage-reducing effect of the test compounds was expressedhere separately for 2 repeats in graded efficacy codes according to thefollowing scheme:

-   -   0: no reduction in damage (appearance corresponding to the        herbicide control)    -   1: slight reduction in damage    -   2: distinct reduction in damage    -   3: significant reduction in damage    -   4: complete reduction in damage (appearance corresponding to the        untreated control)

The trials show clear efficacy of the the inventive compounds selectedby way of example with regard to the reduction in damage to the summerbarley crop plant (HORVS; cv. Montoya) caused by the herbicidemesosulfuron-methyl:

Dose of the Efficacy safener of the of the safener formula (I) Crop(efficacy Example No. (g/ha) plant code) I.40-11 500 HORVS 2 I.40-10 500HORVS 2-3 I.40-10 100 HORVS 2 I.46-10 500 HORVS 2 I.46-10 100 HORVS 2I.48-10 500 HORVS 2-3 I.48-10 100 HORVS 2

What is claimed is:
 1. A compound of general formula (I) or salt thereof

in which R¹ is hydrogen, halogen, cyano, nitro, (C₁-C₆)alkyl,(C₂-C₆)alkenyl, (C₂-C₆)alkynyl, (C₃-C₈)cycloalkyl, (C₃-C₈)cycloalkenyl,(C₁-C₆)alkoxy and (C₁-C₆)alkylS(O)_(p), where the latter seven radicalsare unsubstituted or are substituted by one or more radicals from thegroup of halogen, cyano, (C₁-C₆)alkoxy and (C₁-C₆)alkylS(O)_(p), R² isheteroaryl, where the heteroaryl radical is unsubstituted or substitutedby halogen, cyano, nitro, (C₁-C₆)alkyl, (C₂-C₆)alkenyl, (C₂-C₆)alkynyl,(C₃-C₈)cycloalkyl, (C₃-C₈)cycloalkenyl, (C₁-C₆)alkoxy and(C₁-C₆)alkylS(O)_(p), where the latter seven radicals are unsubstitutedor are substituted by one already more radicals from the group ofhalogen, cyano, (C₁-C₆)alkoxy and (C₁-C₆)alkylS(O)_(p), R³ is hydrogenand (C₁-C₆)alkyl, R⁴ is hydrogen, (C₁-C₁₈)alkyl, (C₁-C₁₈)haloalkyl,(C₁-C₁₈)cyanoalkyl, (C₂-C₁₈)alkenyl, (C₂-C₁₈)alkynyl,(C₃-C₁₂)cycloalkyl, (C₃-C₁₂)cycloalkenyl, aryl, heteroaryl,(C₁-C₁₈)alkoxy-(C₁-C₁₈)alkyl, (C₁-C₁₈)haloalkoxy-(C₁-C₁₈)alkyl,(C₁-C₁₈)alkoxy-(C₁-C₁₈)haloalkyl, (C₁-C₁₈)alkylthio-(C₁-C₁₈)alkyl,(C₁-C₁₈)haloalkylthio-(C₁-C₁₈)alkyl, (C₂-C₁₈)halo alkenyl,(C₂-C₁₈)haloalkynyl, heterocyclyl-(C₁-C₁₈)alkyl, aryl-(C₁-C₁₈)alkyl,(C₃-C₁₂)cycloalkyl-(C₁-C₁₈)alkyl, (C₁-C₁₈)alkoxycarbonyl-(C₁-C₁₈)alkyl,and (C₁-C₁₈)alkoxycarbonyl-(C₃-C₁₂)cycloalkyl-(C₁-C₁₈)alkyl, or aradical of the formula —NR^(a)R^(b) or —N═CR′R^(d), where, in the former2 radicals, each of the R_(a), R_(b), R_(c) and R_(d) radicals isindependently hydrogen, (C₁-C₄)alkyl, (C₂-C₄)alkenyl, (C₂-C₄)alkynyl,benzyl, substituted benzyl, phenyl or substituted phenyl, or R_(a) andR_(b) together with the nitrogen atom may form a 3- to 8-memberedheterocycle which may contain one or two ring heteroatoms from the groupof N, O and S, but not in the case of a 3- or 4-membered heterocycle,and which is unsubstituted or substituted by one or more radicals fromthe group of (C₁-C₄)alkyl and (C₁-C₄)haloalkyl, or R^(c) and R^(d)together with the carbon atom are a 3- to 8-membered carbocyclic orheterocyclic radical which may contain 1 to 3 ring heteroatoms from thegroup of N, O and S, where the carbocyclic or heterocyclic radical isunsubstituted or substituted by one or more radicals from the group of(C₁-C₄)-alkyl and (C₁-C₄)-haloalkyl, n is a number from 0 to 5, and p is0, 1 or
 2. 2. The compound of the general formula (I) as claimed inclaim 1 or salt thereof, in which R¹ is hydrogen, halogen, cyano, nitro,(C₁-C₄)alkyl, (C₂-C₄)alkenyl, (C₂-C₄)alkynyl, (C₃-C₆)cycloalkyl,(C₃-C₆)cycloalkenyl, (C₁-C₄)alkoxy and (C₁-C₄)alkylS(O)_(p), where thelatter seven radicals are unsubstituted or are substituted by onealready more radicals from the group of halogen, cyano, (C₁-C₄)alkoxyand (C₁-C₄)alkylS(O)_(p), R² is heteroaryl, where the heteroaryl radicalis an unsubstituted or substituted by halogen, cyano, nitro,(C₁-C₆)alkyl, (C₂-C₆)alkenyl, (C₂-C₄)alkynyl, (C₃-C₆)cycloalkyl,(C₃-C₆)cycloalkenyl, (C₁-C₆)alkoxy and (C₁-C₄)alkylS(O)_(p), where thelatter seven radicals are unsubstituted or are substituted by onealready more radicals from the group of halogen, cyano, (C₁-C₄)alkoxyand (C₁-C₄)alkylS(O)_(p), R³ is hydrogen and (C₁-C₄)alkyl, R⁴ ishydrogen, (C₁-C₁₆)alkyl, (C₁-C₁₆)haloalkyl, (C₁-C₁₆)cyanoalkyl,(C₂-C₁₆)alkenyl, (C₂-C₁₆)alkynyl, (C₃-C₁₂)cycloalkyl,(C₃-C₁₂)cycloalkenyl, aryl, heteroaryl, (C₁-C₁₆)alkoxy-(C₁-C₁₆)alkyl,(C₁-C₁₆)haloalkoxy-(C₁-C₁₆)alkyl, (C₁-C₁₆)alkoxy-(C₁-C₁₆)haloalkyl,(C₁-C₁₆)alkylthio-(C₁-C₁₆)alkyl, (C₁-C₁₆)haloalkylthio-(C₁-C₁₆)alkyl,(C₂-C₁₆)halo alkenyl, (C₂-C₁₆)haloalkynyl, heterocyclyl-(C₁-C₁₆)alkyl,aryl-(C₁-C₁₆)alkyl, (C₃-C₁₂)cycloalkyl-(C₁-C₁₆)alkyl,(C₁-C₁₆)alkoxycarbonyl-(C₁-C₁₆)alkyl, and(C₁-C₁₆)alkoxycarbonyl-(C₃-C₁₂)cycloalkyl-(C₁-C₁₆)alkyl, n is a numberfrom 0 to 4, and p is 0, 1 or
 2. 3. The compound of the general formula(I) as claimed in claim 1 or salt thereof, in which R¹ is hydrogen,halogen, cyano, methyl, ethyl, CF₃, CF₂Cl, CH₂F, CHF₂, OCH₃, OCF₃, SCH₃,SOCH₃, SO₂CH₃ and SCF₃, R² is heteroaryl, where the heteroaryl radicalis unsubstituted or mono- or polysubstituted by halogen, cyano, methyl,ethyl, CF₃, CF₂Cl, CH₂F, CHF₂, OCH₃, OCF₃, SCH₃, SOCH₃, SO₂CH₃ and SCF₃,R³ is hydrogen, CH₂CH₃ and CH₃, R⁴ is hydrogen, (C₁-C₁₂)alkyl,(C₁-C₁₂)haloalkyl, (C₁-C₁₂)cyanoalkyl, (C₂-C₁₂)alkenyl, (C₂-C₁₂)alkynyl,(C₃-C₁₂)cycloalkyl, (C₃-C₁₂)cycloalkenyl, aryl, heteroaryl,(C₁-C₁₂)alkoxy-(C₁-C₁₂)alkyl, (C₁-C₁₂)haloalkoxy-(C₁-C₁₂)alkyl,(C₁-C₁₂)alkoxy-(C₁-C₁₂)haloalkyl, (C₁-C₁₂)alkylthio-(C₁-C₁₂)alkyl,(C₁-C₁₂)haloalkylthio-(C₁-C₁₂)alkyl, (C₂-C₁₂)haloalkenyl,(C₂-C₁₂)haloalkynyl, heterocyclyl-(C₁-C₁₂)alkyl, aryl-(C₁-C₁₂)alkyl,(C₃-C₁₂)cycloalkyl-(C₁-C₁₂)alkyl, (C₁-C₁₂)alkoxycarbonyl-(C₁-C₁₂)alkyl,and (C₁-C₁₂)alkoxycarbonyl-(C₃-C₁₂)cycloalkyl-(C₁-C₁₂)alkyl, and n is 0,1, 2 or
 3. 4. The of the general formula (I) as claimed in claim 1 orsalt thereof, in which R¹ is hydrogen, fluorine, chlorine, bromine,iodine, CN, methyl, ethyl, CF₃, CF₂Cl, CH₂F, CHF₂, OCH₃, OCF₃, SCH₃,SOCH₃, SO₂CH₃ and SCF₃, R² is pyridin-2-yl, pyridin-3-yl, pyridin-4-yl,pyrazin-2-yl, pyrazin-3-yl, pyrimidin-2-yl, pyrimidin-4-yl,pyrimidin-5-yl, pyridazin-3-yl, pyridazin-4-yl, 1,3,5-triazin-2-yl,1,2,4-triazin-3-yl, 1,2,4-triazin-5-yl, 1,2,4-triazin-6-yl,1,2,3-triazin-4-yl, 1,2,3-triazin-5-yl, 1,2,4-, 1,3,2-, 1,3,6- and1,2,6-oxazinyl, isoxazol-3-yl, isoxazol-4-yl, isoxazol-5-yl,1,3-oxazol-2-yl, 1,3-oxazol-4-yl, 1,3-oxazol-5-yl, isothiazol-3-yl,isothiazol-4-yl, isothiazol-5-yl, 1,3-thiazol-2-yl, 1,3-thiazol-4-yl,1,3-thiazol-5-yl, 1H-pyrrol-1-yl, 1H-pyrrol-2-yl, 1H-pyrrol-3-yl,furan-2-yl, furan-3-yl, thien-2-yl; thien-3-yl, 1H-imidazol-1-yl,1H-imidazol-2-yl, 1H-imidazol-4-yl, 1H-imidazol-5-yl, 1H-pyrazol-1-yl,1H-pyrazol-3-yl, 1H-pyrazol-4-yl, 1H-pyrazol-5-yl,1H-1,2,3-triazol-1-yl, 1H-1,2,3-triazol-4-yl, 1H-1,2,3-triazol-5-yl,2H-1,2,3-triazol-2-yl, 2H-1,2,3-triazol-4-yl, 1H-1,2,4-triazol-1-yl,1H-1,2,4-triazol-5-yl, 4H-1,2,4-triazol-3-yl, 1,2,4-oxadiazol-3-yl,1,2,4-oxadiazol-5-yl, 1,3,4-oxadiazol-2-yl, 1,2,3-oxadiazol-4-yl,1,2,3-oxadiazol-5-yl, 1,2,5-oxadiazol-3-yl, 1,3,4-thiadiazol-2-yl,1,3,4-thiadiazol-5-yl, 1,2,4-thiadiazol-5-yl, 1,2,4-thiadiazol-3-yl,1,2,5-thiadiazol-3-yl, 1,2,5-thiadiazol-3-yl, 1,2,3-thiadiazol-4-yl,1,2,3-thiadiazol-3-yl, which is an unsubstituted or mono- orpolysubstituted by halogen, cyano, methyl, CF₃, CF₂Cl, CH₂F, CHF₂, OCH₃,OCF₃, SCH₃, SOCH₃, SO₂CH₃ and SCF₃, R³ is hydrogen and CH₃, R⁴ ishydrogen, (C₁-C₁₀)alkyl, (C₁-C₁₀)haloalkyl, (C₁-C₁₀)cyanoalkyl,(C₂-C₁₀)alkenyl, (C₂-C₁₀)alkynyl, (C₃-C₉)cycloalkyl,(C₃-C₉)cycloalkenyl, aryl, heteroaryl, (C₁-C₁₀)alkoxy-(C₁-C₁₀)alkyl,(C₁-C₁₀)haloalkoxy-(C₁-C₁₀)alkyl, (C₁-C₁₀)alkoxy-(C₁-C₁₀)haloalkyl,(C₁-C₁₀)alkylthio-(C₁-C₁₀)alkyl, (C₁-C₁₀)haloalkylthio-(C₁-C₁₀)alkyl,(C₂-C₁₈)haloalkenyl, (C₂-C₁₈)haloalkynyl, heterocyclyl-(C₁-C₁₀)alkyl,aryl-(C₁-C₁₀)alkyl, (C₃-C₉)cycloalkyl-(C₁-C₁₀)alkyl,(C₁-C₁₀)alkoxycarbonyl-(C₁-C₁₀)alkyl and(C₁-C₁₀)alkoxycarbonyl-(C₃-C₉)cycloalkyl-(C₁-C₁₀)alkyl, and n is 0, 1, 2or
 3. 5. The compound of the general formula (I) as claimed in claim 1or salt thereof, in which R¹ is hydrogen, fluorine, chlorine, bromine,iodine, cyano, methyl, CF₃, CH₂F, CHF₂, OCH₃, OCF₃, SCH₃, SOCH₃, SO₂CH₃and SCF₃, R² is selected from the group consisting of Q-2.1 to Q-2.60

R³ is hydrogen, R⁴ is hydrogen, methyl, ethyl, n-propyl, i-propyl,n-butyl, n-pentyl, phenyl, benzyl, CH₂(4-Cl-Ph), CH₂(4-F-Ph),CH₂(4-MeO-Ph), 2-methoxyethyl, tetrahydrofuran-2-yl-methyl,tetrahydrofuran-3-ylmethyl, tetrahydropyran-2-ylmethyl,tetrahydropyran-3-ylmethyl, tetrahydropyran-4-ylmethyl,methylpropionate-3-yl, ethylpropionate-3-yl, methylacetate-2-yl,ethylacetate-2-yl, methylpivalate-2-yl, ethylpivalate-3-yl,methyl-2-methyl-propanoate-3-yl, methyl-2,2-dimethylpropanoate-3-yl,ethyl-2-methylpropanoate-3-yl, methyl-2-propanoate-2-yl,ethyl-2-propanoate-2-yl, methylacetate-2-yl, ethylacetate-2-yl,methyl-1-methylcyclopropanecarboxylate-2-yl,ethyl-1-methylcyclopropane-carboxylat-2-yl, 2-(dimethylamino)ethyl,oxetan-3-yl, (3-methyloxetan-3-yl)methyl, 2,2,2-trifluoroethyl,2,2-difluoroethyl, 2-fluoroethyl, 2,2,3,3,3-pentafluoropropyl,cyclopropylmethyl, 1-cyclopropylethyl, (1-methylcyclopropyl)methyl,(2,2-dichloro-cyclopropyl)methyl, (2,2-dimethylcyclopropyl)methyl,allyl, propargyl (prop-2-yn-1-yl), 2-chloroprop-2-en-1-yl,3-phenylprop-2-yn-1-yl, 3,3-dichloroprop-2-en-1-yl,3,3-di-chloro-2-fluoroprop-2-en-1-yl, methylprop-2-yn-1-yl,2-methylprop-2-en-1-yl, but-2-en-1-yl, but-3-en-1-yl, but-2-yn-1-yl,but-3-yn-1-yl, 4-chlorobut-2-yn-1-yl, 3-methylbut-2-en-1-yl,3-methylbut-1-en-1-yl, 1-(2E)-1-methylbut-2-en-1-yl, (E)-pent-3-en-2-ylor (Z)-pent-3-en-2-yl, cyclobutylmethyl, cyclopentylmethyl,cyclohexylmethyl, heptan-2-yl, isobutyl, 1,3-dioxolan-2-ylmethyl or1-ethyl-5-methyl-1H-pyrazole-4-methyl, n is 0, 1, 2 or
 3. 6. Thecompound of the general formula (I) as claimed in claim 1 or saltthereof, in which (R¹)_(n)-phenyl is selected from the group consistingof Q-1.1 to Q-1.53

and R² is selected from the group consisting of Q-2.1 to Q-2.60

R³ is hydrogen, and R⁴ is hydrogen, methyl, ethyl, n-propyl, i-propyl,n-butyl, n-pentyl, phenyl, benzyl, CH₂(4-Cl-Ph), CH₂(4-F-Ph),CH₂(4-MeO-Ph), 2-methoxyethyl, tetrahydrofuran-2-yl-methyl,tetrahydrofuran-3-ylmethyl, tetrahydropyran-2-ylmethyl,tetrahydropyran-3-ylmethyl, tetrahydropyran-4-ylmethyl,methylpropionate-3-yl, ethylpropionate-3-yl, methylacetate-2-yl,ethylacetate-2-yl, methylpivalate-2-yl, ethylpivalate-3-yl,methyl-2-methyl-propanoate-3-yl, methyl-2,2-dimethylpropanoate-3-yl,ethyl-2-methylpropanoate-3-yl, methyl-2-propanoate-2-yl,ethyl-2-propanoate-2-yl, methylacet-2-yl, ethylacet-2-yl,methyl-1-methylcyclopropanecarboxylate-2-yl,ethyl-1-methylcyclopropanecarboxylat-2-yl, 2-(dimethylamino)ethyl,oxetan-3-yl, (3-methyloxetan-3-yl)methyl, 2,2,2-trifluoroethyl,2,2-difluoroethyl, 2-fluoroethyl, 2,2,3,3,3-pentafluoropropyl,cyclopropyl-methyl, 1-cyclopropylethyl, (1-methylcyclopropyl)methyl,(2,2-dichlorocyclo-propyl)methyl, (2,2-dimethylcyclopropyl)methyl,allyl, propargyl (prop-2-yn-1-yl), 2-chloroprop-2-en-1-yl,3-phenylprop-2-yn-1-yl, 3,3-dichloroprop-2-en-1-yl,3,3-dichloro-2-fluoroprop-2-en-1-yl, methylprop-2-yn-1-yl,2-methylprop-2-en-1-yl, but-2-en-1-yl, but-3-en-1-yl, but-2-yn-1-yl,but-3-yn-1-yl, 4-chlorobut-2-yn-1-yl, 3-methylbut-2-en-1-yl,3-methylbut-1-en-1-yl, 1-(2E)-1-methylbut-2-en-1-yl, (E)-pent-3-en-2-ylor (Z)-pent-3-en-2-yl, cyclobutylmethyl, cyclopentylmethyl,cyclohexylmethyl, heptan-2-yl, isobutyl, 1,3-dioxolan-2-ylmethyl or1-ethyl-5-methyl-1H-pyrazole-4-methyl.
 7. The compound of the generalformula (I) as claimed in claim 1 or salt thereof, in which(R¹)_(n)-phenyl is selected from the group consisting of Q-1.1 to Q-1.53

and R² is selected from the group consisting of Q-2.1 to Q-2.60

R³ is hydrogen, and R⁴ is hydrogen, methyl, ethyl, n-propyl, i-propyl,n-butyl, n-pentyl, phenyl, benzyl, CH₂(4-Cl-Ph), CH₂(4-F-Ph),CH₂(4-MeO-Ph), 2-methoxyethyl, tetrahydrofuran-2-yl-methyl,tetrahydrofuran-3-ylmethyl, tetrahydropyran-2-ylmethyl,tetrahydropyran-3-ylmethyl, tetrahydropyran-4-ylmethyl,methylpropionate-3-yl, ethylpropionate-3-yl, methylacetate-2-yl,ethylacetate-2-yl, methylpivalate-2-yl, ethylpivalate-3-yl,methyl-2-methyl-propanoate-3-yl, methyl-2,2-dimethylpropanoate-3-yl,ethyl-2-methylpropanoate-3-yl, methyl-2-propanoate-2-yl,ethyl-2-propanoate-2-yl, methylacet-2-yl, ethylacet-2-yl,methyl-1-methylcyclopropanecarboxylate-2-yl,ethyl-1-methylcyclopropanecarboxylat-2-yl, 2-(dimethylamino)ethyl,oxetan-3-yl, (3-methyloxetan-3-yl)methyl, 2,2,2-trifluoroethyl,2,2-difluoroethyl, 2-fluoroethyl, 2,2,3,3,3-pentafluoropropyl,cyclo-propylmethyl, 1-cyclopropylethyl, (1-methylcyclopropyl)methyl,(2,2-dichloro-cyclopropyl)methyl, (2,2-dimethylcyclopropyl)methyl,allyl, propargyl (prop-2-yn-1-yl), 2-chloroprop-2-en-1-yl,3-phenylprop-2-yn-1-yl, 3,3-dichloroprop-2-en-1-yl,3,3-dichloro-2-fluoroprop-2-en-1-yl, methylprop-2-yn-1-yl,2-methylprop-2-en-1-yl, but-2-en-1-yl, but-3-en-1-yl, but-2-yn-1-yl,but-3-yn-1-yl, 4-chlorobut-2-yn-1-yl, 3-methylbut-2-en-1-yl,3-methylbut-1-en-1-yl, 1-(2E)-1-methylbut-2-en-1-yl, (E)-pent-3-en-2-ylor (Z)-pent-3-en-2-yl, cyclobutylmethyl, cyclopentylmethyl,cyclohexylmethyl, heptan-2-yl, isobutyl, 1,3-dioxolan-2-ylmethyl or1-ethyl-5-methyl-1H-pyrazole-4-methyl.
 8. A plant-protectingcomposition, comprising: at least one compound of the general formula(I) or salts thereof as claimed in claim 1; and at least oneagrochemical.
 9. The composition as claimed in claim 8, comprising atleast one herbicide.
 10. A method of reducing phytotoxic effects ofpesticides on plants, the method comprising use of one or more compoundsof claim 1 or of the composition as claimed in claim
 8. 11. A method ofreducing phytotoxic effects of pesticides on plants, the methodcomprising: use of one or more compounds of the general formula (I) asclaimed in claim 1; and use of pesticides deployed simultaneously orsequentially.
 12. The method as claimed in claim 11, wherein thepesticides are one or more herbicides.
 13. The method as claimed inclaim 11, characterized in that compounds of the formula (I) or saltsthereof as claimed in claim 1 are applied to the plants, parts of theplants, or seeds or seed material thereof.
 14. The composition asclaimed in claim 8, further comprising at least one formulationauxiliary.
 15. The method of claim 10, further comprising use of atleast one herbicide.
 16. The method of claim 13, further comprising useof at least one herbicide.